138513-21-0Relevant articles and documents
Conduramine F-1 epoxides: synthesis and their glycosidase inhibitory activities
?ysek, Robert,Favre, Sylvain,Vogel, Pierre
, p. 6558 - 6572 (2007)
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
Asymmetric total synthesis of (?)-conduramine A-1 via a chiral syn,anti-oxazine
Myeong, In-Soo,Kim, Jin-Seok,Lee, Yong-Taek,Kang, Jong-Cheol,Park, Seok-Hwi,Jung, Changyoung,Ham, Won-Hun
, p. 823 - 828 (2016)
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.
Synthesis of (-)-Conduramine A1, (-)-Conduramine A2 and (-)-Conduramine E2 in Six Steps from Cyclohexa-1,4-diene
Da Silva Pinto, Solange,Davies, Stephen G.,Fletcher, Ai M.,Roberts, Paul M.,Thomson, James E.
, p. 7933 - 7937 (2019/10/10)
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.
Syntheses of optically pure conduramines via the strategy of hetero diels-alder reaction of masked o -benzoquinones with homochiral nitroso dienophiles
Lu, Ping-Hsun,Yang, Ching-Shun,Devendar, Badugu,Liao, Chun-Chen
supporting information; experimental part, p. 2642 - 2645 (2010/08/22)
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, (+)-
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
Chang, Yuan-Kang,Lo, Hong-Jay,Yan, Tu-Hsin
supporting information; experimental part, p. 4278 - 4281 (2010/01/16)
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.
Search for α-glucosidase inhibitors: New N-substituted valienamine and conduramine F-1 derivatives
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
, p. 6255 - 6282 (2007/10/03)
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.
Total asymmetric synthesis of (-)-conduramine B-1 and of its enantiomer. N-Benzyl derivatives of conduramine B-1 are β-glucosidase inhibitors
Lysek, Robert,Schuetz, Catherine,Vogel, Pierre
, p. 3071 - 3075 (2007/10/03)
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.
(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
Lysek, Robert,Schuetz, Catherine,Vogel, Pierre
, p. 2788 - 2811 (2007/10/03)
(-)- 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
Synthesis of conduramines from N-tert-butoxycarbonylpyrrole
Leung-Toung, Regis,Liu, Yanzhou,Muchowski, Joseph M.,Wu, Yu-Lin
, p. 3235 - 3250 (2007/10/03)
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.
Synthesis of (+/-)-Conduramines from Pyrrole
Leung-Toung, Regis,Liu, Yanzhou,Muchowski, Joseph M.,Wu, Yu-Lin
, p. 1639 - 1642 (2007/10/02)
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).
