- Synthesis of (-)-Conduramine A1, (-)-Conduramine A2 and (-)-Conduramine E2 in Six Steps from Cyclohexa-1,4-diene
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A method to enable the synthesis of conduramines and their N-substituted derivatives (enantiopure or racemic form) in six steps (five steps for N-substituted derivatives) from cyclohexa-1,4-diene is reported. Key features of this reaction sequence include a preparation of benzene oxide that is amenable to multigram scale, and its efficient ring-opening upon treatment with a primary amine. Epoxidation of the resultant amino alcohols (40% aq HBF4 then m-CPBA) is accompanied by hydrolytic ring-opening in situ to give the corresponding N-substituted conduramine derivatives directly. These may undergo subsequent N-deprotection to give the parent conduramines, as demonstrated by the preparation of enantiopure (-)-conduramine A1, (-)-conduramine A2, and (-)-conduramine E2 (the latter two for the first time). The selectivity of the epoxidation reaction is proposed to be the result of competitive ammonium-directed and hydroxyl-directed epoxidation processes, followed by either direct (SN2-type) or conjugate (SN2′-type) ring-openings of the intermediate epoxides.
- Da Silva Pinto, Solange,Davies, Stephen G.,Fletcher, Ai M.,Roberts, Paul M.,Thomson, James E.
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p. 7933 - 7937
(2019/10/10)
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- Efficient enantiospecific synthesis of ent-conduramine F-1
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An efficient enantiospecific total synthesis of ent-conduramine F-1 (aminocyclohexenetriol) was accomplished starting from the bis-Weinreb amide of tartaric acid. Key reactions in the synthesis include the desymmetrization of tartaric acid amide with viny
- Prasad, Kavirayani R.,Rangari, Vipin Ashok
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p. 6689 - 6693
(2018/10/15)
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- Asymmetric total synthesis of (?)-conduramine A-1 via a chiral syn,anti-oxazine
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The total synthesis of (?)-conduramine A-1 was achieved by using a diastereomerically enriched syn,anti-oxazine intermediate. The key steps in this strategy were the stereoselective extension of the chirality of syn,anti-oxazine, a Wittig reaction, and a ring-closing metathesis reaction.
- Myeong, In-Soo,Kim, Jin-Seok,Lee, Yong-Taek,Kang, Jong-Cheol,Park, Seok-Hwi,Jung, Changyoung,Ham, Won-Hun
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p. 823 - 828
(2016/09/02)
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- A Chiron Approach to Diversity-Oriented Synthesis of Aminocyclitols, (-)-Conduramine F-4 and Polyhydroxyaminoazepanes from a Common Precursor
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The total syntheses of aminocyclitols, (-)-conduramine F-4, and polyhydroxyaminoazepanes have been achieved from a common precursor derived from tri-O-benzyl-d-glucal through a 'diversity-oriented' approach. Tri-O-benzyl-d-glucal was converted into a protected 1,6-diol through a sequence of steps that include transformation to a 2-tosylamidoglucose derivative, selective deprotection of primary C-6 benzyloxy group, LiAlH4-mediated one-step reduction of acetate groups, and reductive ring opening of the resulting hemiacetal as the key steps. The 1,6-diol served as a common precursor in our diversity oriented approach toward the target molecules. Mesylation of the diol followed by double nucleophilic substitution reaction with primary amines led to the synthesis of amino-substituted polyhydroxyazepanes. On the other hand, dialdehyde obtained from the oxidation of 1,6-diol was found to be a convenient starting material for the synthesis of aminocyclitols and (-)-conduramine F-4. McMurry coupling of the dialdehyde was successfully employed, for the first time, to construct the carbocyclic framework of aminoyclitols, while bis-Wittig olefination of the dialdehyde followed by Grubb's(II)-catalyzed RCM delivered (-)-conduramine F-4. The stereochemistry of newly created chiral centers in aminocyclitols was established through single crystal X-ray crystallography and detailed NOE studies.
- Harit, Vimal Kant,Ramesh, Namakkal G.
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p. 11574 - 11586
(2016/12/09)
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- Dearomative dihydroxylation with arenophiles
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Aromatic hydrocarbons are some of the most elementary feedstock chemicals, produced annually on a million metric ton scale, and are used in the production of polymers, paints, agrochemicals and pharmaceuticals. Dearomatization reactions convert simple, readily available arenes into more complex molecules with broader potential utility, however, despite substantial progress and achievements in this field, there are relatively few methods for the dearomatization of simple arenes that also selectively introduce functionality. Here we describe a new dearomatization process that involves visible-light activation of small heteroatom-containing organic molecules - arenophiles - that results in their para-cycloaddition with a variety of aromatic compounds. The approach uses N-N-arenophiles to enable dearomative dihydroxylation and diaminodihydroxylation of simple arenes. This strategy provides direct and selective access to highly functionalized cyclohexenes and cyclohexadienes and is orthogonal to existing chemical and biological dearomatization processes. Finally, we demonstrate the synthetic utility of this strategy with the concise synthesis of several biologically active compounds and natural products.
- Southgate, Emma H.,Pospech, Jola,Fu, Junkai,Holycross, Daniel R.,Sarlah, David
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p. 922 - 928
(2016/09/28)
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- Stereoselective synthesis of (-)-conduramine C-1 and (-)-conduramine D-1
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A highly stereoselective approach to aminocyclohexenetriols conduramine C-1 1 and conduramine D-1 2 has been described. Conduramines are structural units of some biologically active natural products such as (+)-lycoricidine and (+)-narciclasine. The strategy developed by us for their synthesis is general in nature to make related skeletons and also the molecules containing conduramine structural unit. The key reactions are Grignard addition on glycosylamine, ring closing metathesis (RCM), and Mitsunobu inversion.
- Rajender, Anugula,Rao, Batchu Venkateswara
-
supporting information
p. 2329 - 2331
(2013/06/27)
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- Remarkable stereoselectivity in intramolecular Borono-Mannich reactions: Synthesis of conduramines
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An unprecedented intramolecular Petasis condensation provides a novel approach to biologically important conduramines. The compounds are produced with an exclusive anti stereoselectivity for the newly created β-amino alcohol motif. The stereochemical outc
- Norsikian, Stephanie,Soule, Jean-Francois,Cannillo, Alexandre,Guillot, Regis,Tran Huu Dau, Marie-Elise,Beau, Jean-Marie
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p. 544 - 547
(2012/03/26)
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- Syntheses of optically pure conduramines via the strategy of hetero diels-alder reaction of masked o -benzoquinones with homochiral nitroso dienophiles
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Highly stereoselective hetero Diels-Alder reactions of masked o-benzoquinones (MOBs) with homochiral nitroso dienophiles are described along with their application in the syntheses of (+)-ent-conduramine F-1, (+)-conduramine E-1, (-)-conduramine A-1, (+)-
- Lu, Ping-Hsun,Yang, Ching-Shun,Devendar, Badugu,Liao, Chun-Chen
-
supporting information; experimental part
p. 2642 - 2645
(2010/08/22)
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- Formal total synthesis of (±)-conduramine E utilising the Bryce-Smith-Gilbert photoamination reaction
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Utilising a Bryce-Smith-Gilbert photoamination of benzene as a key step, a synthesis of (±)-conduramine E was carried out. A highly regioselective dihydroxylation of a cyclic diene was effected utilising Sharpless AD-mix-β. Georg Thieme Verlag Stuttgart.
- Chappell, David,Drew, Michael G.B.,Gibson, Shane,Harwood, Laurence M.,Russell, Andrew T.
-
body text
p. 517 - 520
(2010/09/11)
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- A flexible strategy based on a C2-symmetric pool of chiral substrates: Concise synthesis of (+)-valienamine, key intermediate of (+)- pancratistatin, and conduramines A-1 and E
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A new strategy invoking a new application of the [3,3] sigmatropic rearrangement of allylic azides and the presence of a C2 symmetry element within a pool of chiral substrates was evolved. Not only does this simple flexible strategy provide a concise approach to (+)-valienamine, but it also can readily be adopted for the synthesis of conduramines A-1 and E and the enantiopure azido carbonate 4, a key intermediate of (+)-pancratistatin.
- Chang, Yuan-Kang,Lo, Hong-Jay,Yan, Tu-Hsin
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supporting information; experimental part
p. 4278 - 4281
(2010/01/16)
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- Use of enantiomerically pure 7-azabicyclo[2.2.1]heptan-2-ol as a chiral template for the synthesis of aminocyclitols
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(Chemical Equation Presented) Using enantiopure 7-azabicyclo[2.2.1]heptane- 2-ol, the synthesis of cis- as well as trans-2-aminocyclohexanols, dihydroconduramine E-1, and ent-conduramine F-1 has been described.
- Pandey, Ganesh,Tiwari, Keshri Nath,Puranik
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scheme or table
p. 3611 - 3614
(2009/05/07)
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- Chemoenzymatic synthesis and biological evaluation of (-)-conduramine C-4
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Previously unreported (-)-conduramine C-4 was synthesized in six steps from a bacterial bromobenzene metabolite in 23% overall yield. The chemoenzymatic route involved toluene dioxygenase dihydroxylation, β-epoxidation, epoxide ring-opening, Staudinger reduction, radical debromination, and Amberlite- catalyzed hydrolysis. (-)-Conduramine C-4 and other related compounds synthesised were assayed for galactosidase-activity inhibition against β-D-galactoside galactohidrolase isolated from Aspergillus oryzae. Copyright Taylor & Francis Group, LLC.
- Bellomo, Ana,Giacomini, Cecilia,Brena, Beatriz,Seoane, Gustavo,Gonzalez, David
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p. 3509 - 3518
(2008/03/13)
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- Conduramine F-1 epoxides: synthesis and their glycosidase inhibitory activities
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Starting from (±)-7-oxanorbornenone ((±)-14), (±)-(1RS,2RS,3SR,6SR)-6-azidocyclohex-4-en-1,2,3-triol ((±)-24) and (±)-(1RS,2RS,3SR,6RS)-6-azidocyclohex-4-en-1,2,3-triol ((±)-26) were obtained. Epoxidation of the latter cyclohexene derivative gave two epox
- ?ysek, Robert,Favre, Sylvain,Vogel, Pierre
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p. 6558 - 6572
(2008/02/05)
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- Search for α-glucosidase inhibitors: New N-substituted valienamine and conduramine F-1 derivatives
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A solid-phase synthesis of new N-substituted valienamines has been developed and new synthesis of (±)-conduramine F-1, (-)-conduramine F-1, and (+)-ent-conduramine F-1 is presented, together with the preparation of N-benzylated conduramines F-1. N-Benzylation of both valienamine and (+)-ent-conduramine F-1 improves their inhibitory activity toward α-glucosidases significantly. The additional hydroxymethyl group makes valienamine derivatives more active than their (+)-ent-conduramine F-1 analogues.
- Lysek, Robert,Schuetz, Catherine,Favre, Sylvain,O'Sullivan, Anthony C.,Pillonel, Christian,Kruelle, Thomas,Jung, Pierre M.J.,Clotet-Codina, Imma,Este, Jose A.,Vogel, Pierre
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p. 6255 - 6282
(2007/10/03)
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- (1S,2S,3R,6R)-6-aminocyclohex-4-ene-1,2,3-triol (=(-)-conduramine B-1) is a selective inhibitor of α-mannosidases. Its inhibitory activity is enhanced by N-benzylation
-
(-)- and (+)-Conduramine B-1 ((-)- and (+)-5, resp.) have been derived from (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one ('naked sugars' of the first generation). Although (-)-5 imitates the structure of β-glucosides, it does not inhibit β-glucosidases
- Lysek, Robert,Schuetz, Catherine,Vogel, Pierre
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p. 2788 - 2811
(2007/10/03)
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- Total asymmetric synthesis of (-)-conduramine B-1 and of its enantiomer. N-Benzyl derivatives of conduramine B-1 are β-glucosidase inhibitors
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The 'naked sugars' (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one have been converted into (-)-conduramine B-1 ((-)-3) and its enantiomer (+)-3, respectively. They have been condensed with a variety of aldehydes in the presence of NaBH(OAc)3.
- Lysek, Robert,Schuetz, Catherine,Vogel, Pierre
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p. 3071 - 3075
(2007/10/03)
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- From cycloolefins to chiral, polyfunctionalized linear C6/C12 building blocks - Biocatalysis, (-)-conduramine E
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1,4-Cyclohexadiene is the starting material for the expeditious synthesis of the 1S2S3S4R- and 1R2R3R4S-epoxy-cyclohexene-1,4-diol monoacetates through enzyme-catalyzed hydrolysis and transesterification, respectively. The absolute configurations are established by correlation of (-)-10 and known (+)-conduramine E. Ozonation and functional group manipulation open access to fully protected, polyfunctionalized C6-aldehydes whose reductive coupling to C2-symmetrical C12 building blocks is being explored. (C) 2000 Elsevier Science Ltd.
- Spielvogel,Kammerer,Keller,Prinzbach
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p. 7863 - 7867
(2007/10/03)
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- A synthesis of conduramine B and a 'condurithiol', useful molecules for studying the inhibition of β-xylosidases
-
Conduramine B and a 'condurithiol', namely (1S,2S,3R,6R)-6-aminocyclohex-4-ene-1,2,3-triol and 1R,2S,3R,6R)-6-sulfanylcyclohex-4-ene-1,2,3-triol, have been prepared by the thermal rearrangement of an acetimidate and a dithiocarbonate, respectively. Both the amine and the thiol are putative inhibitors of β-xylosidases and, in order to mimic the natural substrate more closely, an N- and an S-pseudo-disaccharide have been prepared.
- McDonough, Matthew J.,Stick, Robert V.,Tilbrook, D. Matthew G.
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p. 143 - 147
(2007/10/03)
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- Synthesis of conduramines from N-tert-butoxycarbonylpyrrole
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Two related synthetic strategies were devised to convert the Diels- Alder adduct 3c of Boc-pyrrole and p-toluenesulfonylacetylene into various racemic and optically pure conduramines. One process consists of the regio- and stereoselective hydroxylation of 3c to the tri- and dihydroxylated azabicyclo-[2.2.1]heptane derivatives 10b (Scheme 2) and the exo-endo mixture 13-14 (Scheme 3). Anionic fragmentation of 10b (methylmagnesium bromide) and of the 13-14 sulfone mixture (lithium bis-(trimethylsilyl)amide) generated the corresponding tri- and dihyroxylated aminocyclohexenes 17 and 16 (Scheme 3). Compound 17 is an aminocyclitol with a stereochemistry and partial aminotriol sequence identical to that found in neoinosamine. Compound 16 served as a source of the protected and free aminodiols 35b and 35a (Scheme 6), which were stereospecifically epoxidized to 36 (Scheme 6) and 40 (Scheme 7). Phenylselenide cleavage of these epoxides provided 37 (Scheme 6) and 41a (Scheme 7), which after selenoxide cycloelimination and protecting group manipulation were converted into (±)-conduramine C-1 (39a, Scheme 6) and the previously unreported, all-cis-conduramine D-1 (43a, Scheme 7). In a second process, anionic fragmentation of the bicyclic system is effected prior to introduction of the hydroxyl groups, as exemplified by the high-yielding conversion of the exo-endo mixture of azabicycloheptenes 11 and 12 into the aminocyclohexadiene 15 (Scheme 3). Osmate catalyzed cis-dihydroxylation of the derived bis-Boc derivative 20 (Scheme 4) led stereospecifically to the α-cis-diol 21 which was transformed into (±)-conduramine A-1 (27a) and its tetraacetyl derivative 27b via the epoxy compound 24. On the other hand, peracid oxidation of the diene 15 gave the β-epoxide 28 (Scheme 5) which was cleaved to the trans-diol 29 with aqueous sulfuric acid. This diol was converted into (±)-conduramine F-1 (34a) and its tetraacetyl derivative (34b) by a reaction sequence similar to that used for the other conduramine syntheses. Fractional crystallization of the diastereomeric mixture of Michael adducts obtained from (±)-3c and (-)-methyl lactate gave (-)-44a and (-)-45a both in ≤47% yield (Scheme 8). Both the carboxylic acid (+)-44b and the primary alcohol (+)-46 derived from (-)-44a were converted into (-)-3c with excess methylmagnesium bromide (ca. 40% overall yield). In the same way (-)-45a was transformed into optically pure (+)-3c. (-)-3c and (+)-3c were then converted into (-)-conduramine C-1 [(-)-39a] and (+)-conduramine D-1 [(+)-43a] by procedures identical to those used for the racemic compounds.
- Leung-Toung, Regis,Liu, Yanzhou,Muchowski, Joseph M.,Wu, Yu-Lin
-
p. 3235 - 3250
(2007/10/03)
-
- Total synthesis of acanthacerebroside A and astrocerebroside A via a chiral epoxide intermediate derived from L-quebrachitol
-
The chiral and stereoselective total synthesis of novel cerebrosides, acanthacerebroside A (1) and astrocerebroside A (2), isolated from starfish, is described. The phytosphingosine moieties in 1 and 2 were prepared by the coupling reaction of dialkylmagnesium reagents with the common epoxide intermediate, 2-(t-butoxycarbonyl)amino-1-O-(t-butyldiphenylsilyl)-2-deoxy- 3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol (5). The epoxide (5) was synthesized from naturally occurring cyclitol, L-quebrachitol via the conduramine derivative, which was prepared regio- and stereoselectively by the Pd-catalyzed azidation of the allyl carbonate derivative. Condensation of phytosphingosines with 2-acetoxy fatty acid residue, followed by glycosidation, furnished the total synthesis. This work established an effective synthetic pathway to a wide variety of cerebrosides containing various phytosphingosines and 2-hydroxy fatty acid residue; the first total synthesis of astrocerebroside A (2) fully confirmed the proposed structure.
- Chida, Noritaka,Sakata, Noboru,Murai, Katsuyuki,Tobe, Takahiko,Nagase, Toshihiko,Ogawa, Seiichiro
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p. 259 - 272
(2007/10/03)
-
- Desymmetrisation of dienylsilanes. Stereoselective access to cyclitols and carba-sugars
-
The diastereo- and enantioselective functionalisation of 1,4-cyclohexadienylsilanes using Sharpless asymmetric dihydroxylation and aminohydroxylation offers a straightforward access to various classes of potent inhibitors of glycosidases. The scope and limitation of this desymmetrisation method is illustrated here with the synthesis of various conduritols, carba-sugars and carba-C-disaccharides.
- Landais, Yannick
-
p. 104 - 111
(2007/10/03)
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- An efficient enzymatic preparation of (+)- and (-)-conduritol E, a cyclitol with C2 symmetry
-
Lypozyme IM (immobilised lipase from Mucor miehei) catalyses the enantiomeric alcoholysis of tetraacetylconduritol E (±)-2 to give enantiopure (1R,2R,3R,4R)-tetrahydroxycyclohex-5-ene (-)-1, and the unreacted ester (1S,2S,3S,4S)-tetraacetyloxycyclohex-5-ene, (+)-2. The latter was transformed by basic hydrolysis into (+)-1 in high yield and 95% ee. Selective amination of partial ester (-)-3, obtained by short alcoholysis of (±)-2, furnished the previously unreported conduramine F-4, (-)-4.
- Sanfilippo, Claudia,Patti, Angela,Piattelli, Mario,Nicolosi, Giovanni
-
p. 1569 - 1573
(2007/10/03)
-
- Enzymatic desymmetrisation of conduritol D. Preparation of homochiral intermediates for the synthesis of cyclitols and aminocyclitols
-
From meso-conduritol D tetraacetate four homochiral partial derivatives, namely (+)-(1R,2R,3S,4S)-1-hydroxy-2,3,4-triacetoxy-5-cyclohexene, (-)-(1R,2R,3S,4S)-2-hydroxy-1,3,4-triacetoxy-5-cyclohexene, (-)-(1R,2R,3S,4S)-1-benzyloxy-3,4-diacetoxy-2-hydroxy-5-cyclohexene and (+)-(1R,2R,3S,4S)-3,4-diacetoxy-1,2-dihydroxy-5-cyclohexene, have been prepared through enzymatic reactions catalysed by one of the following lipases: from porcine pancreas, from Mucor miehei and from Candida cylindracea. These compounds are of potential utility in the synthesis of cyclitols and aminocyclitols. As an example, the preparation of the previously unreported (+)-conduramine C-4 is also reported.
- Patti, Angela,Sanfilippo, Claudia,Piattelli, Mario,Nicolosi, Giovanni
-
p. 2665 - 2670
(2007/10/03)
-
- On the flexibility of allylic azides as synthetic intermediates
-
Asymmetric synthesis of an allylic azide combined with the facility of the [3.3]sigmatropic rearrangement provides a simple strategy for the synthesis of conduramine E.
- Trost,Trost, Barry M.,Pulley,Pulley, Shon R.
-
p. 8737 - 8740
(2007/10/02)
-
- Stereospecific synthesis of conduramine-F4 and conduritol-F (Leucanthemitol)
-
Stereospecific synthesis of Conduramine-F4 and Conduritol-F has been achieved by fully stereospecific cyloaddition of singlet oxygen to cyclohexadiene ketal 1 followed by reductive extrusion of one oxygen atom. The obtained monoepoxide 3 has be
- Secen,Gultekin,Sutbeyaz,Balci
-
p. 2103 - 2108
(2007/10/02)
-
- Synthesis of (+/-)-Conduramines from Pyrrole
-
The Diels-Alder product 1b, of tosylacetylene and N-tert-Boc-pyrrole, was converted into (+/-)-conduramine C-1 (22) and the tetraacetates of (+/-)-conduramine A-1 (9b) and F-1 (15b).
- Leung-Toung, Regis,Liu, Yanzhou,Muchowski, Joseph M.,Wu, Yu-Lin
-
p. 1639 - 1642
(2007/10/02)
-
- Enantioselective synthesis of (-)-conduramine C1 and aminobromocyclitol derivatives
-
(1S,2R,6R,7R)-4-Phenyl-3-10-dioxa-5-azatricyclo[5.2.1.02,6]dec-4-en -9-one ((+)-5) obtained in 6 steps from the Diels-Alder adduct of furan to 1-cyanovinyl (1S)-camphanate ((+)-3) was reduced to the corresponding endo-alcohol (+)-6 the treatmen
- Allemann,Vogel
-
-
- INTRAMOLECULAR AMINO DELIVERY REACTIONS FOR THE SYNTHESIS OF VALIENAMINE AND ANALOGUES
-
Iodocyclization and sigmatropic rearrangement reactions of N-substituted carbonimidothioates are used to prepare valienamine (1), 7-norvalienamine (8), and the valienamine-based pseudo-disaccharide 12. Key words: carbonimidothioates; iodocyclization; rearrangement; glucosidase inhibitors; pseudo disaccharides
- Knapp, Spencer,Naughton, Andrew B. J.,Dhar, T. G. Murali
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p. 1025 - 1028
(2007/10/02)
-
- (±)-6-acetamido-1,2-anhydro-6-deoxy-myo-inositol: A tight-binding inhibitor and pseudosubstrate for N-acetyl-β-glucosaminidases
-
A five-step procedure is described for the synthesis of the title compound (N-acetylconduramine B trans-epoxide, 14) from tetra-O-acetylconduritol B [(±)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol]. Inhibition studies with N-acetyl-β-gl
- Legler,Bollhagen
-
p. 113 - 123
(2007/10/02)
-
- Asymmetric Synthesis of cis-1,3-Diamino-1,3-dideoxycyclitols
-
Starting with the hetero-Diels-Alder reaction of the O-isopropylidene-protected cis-cyclohexa-3,5-diene-1,2-diol with (-)-2,3:5,6-di-O-isopropylidene-1-nitroso-α-D-manno-furanosyl chloride the optically pure (+)-endo-adduct was exclusively formed.After re
- Schuerrle, Karsten,Beier, Barbara,Piepersberg, Wolfgang
-
p. 2407 - 2412
(2007/10/02)
-
- Asymmetric Induction of Four Chiral Centers by Hetero Diels-Alder Reaction of a Chiral Nitroso Dienophile
-
The Diels-Alder reaction of cis-5,6-diacetoxy-1,3-cyclohexadiene (1), which has a meso configuration, with the chiral nitroso dienophile 2 occurs with induction of four asymmetric centers in very high optical yield (ee = 94percent) and leads to the dihydr
- Werbitzky, Oleg,Klier, Konrad,Felber, Helena
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p. 267 - 270
(2007/10/02)
-
- Cyclitol Reactions, IV. Synthesis of Enantiomeric Conduritols and Amino-Conduritols
-
The key-intermediate for all syntheses described in this paper is the 1-O-tosylate 7 of quebrachitol (1).This leads, via 8, to the 1L-conduritol B (5) and, via 13, to the 1L-conduritol F (17).Selective displacement of the equatorial tosyloxy group in comp
- Paulsen, Hans,Roeben, Wolfgang,Heiker, Fred R.
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p. 3242 - 3252
(2007/10/02)
-