- Concise synthesis of (+)-conduritol F and inositol analogues from naturally available (+)-proto-quercitol and their glucosidase inhibitory activity
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An effective synthesis of (+)-conduritol F, (+)-chiro- and (+)-epi-inositols from naturally available (+)- proto-quercitol is described. This synthetic method provides a concise synthesis of cyclitols in enantiomerically pure form. Of the synthesized cyclitols, (+)-conduritol F potently inhibits type I α-glucosidase with an IC50 value of 86.1 lM, which is five times greater than the standard antidiabetic drug, acarbose.
- Worawalai, Wisuttaya,Rattanangkool, Eakkaphon,Vanitcha, Avassaya,Phuwapraisirisan, Preecha,Wacharasindhu, Sumrit
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p. 1538 - 1540
(2012/04/04)
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- Common-intermediate strategy for synthesis of conduritols and inositols via beta-hydroxy cyclohexenylsilanes.
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[reaction: see text] Syntheses of conduritols B-D and F and d-(+)-chiro- and neo-inositols from cyclohexenylsilane intermediates are described. The key cyclohexylsilane intermediates 5 and 14 were synthesized by stereoselective olefin dihydroxylation of t
- Heo, Jung-Nyoung,Holson, Edward B,Roush, William R
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p. 1697 - 1700
(2007/10/03)
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- Facile syntheses of all possible diastereomers of conduritol and various derivatives of inositol stereoisomers in high enantiopurity from myo-inositol
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Phosphoinositide-based signaling processes are crucially important in intracellular signal transduction events. Inositol phosphate analogues have been useful in probing the structure-activity relationships between inositol phosphates and biomacromolecules, and in studying biological functions of newly found inositol phosphates. Thus, a systematic and ready access to inositol stereoisomers is highly desirable. And practical and convenient syntheses of conduritols and related compounds are also important because of their biological activities and their synthetic utilities in the preparation of other bioactive molecules. We herein report the first syntheses of all possible diastereomers of conduritol and various derivatives of eight inositol stereoisomers in high enantiopurity from myo-inositol, which involve efficient enzymatic resolution of the intermediates conduritol B and C derivatives, followed by oxidation-reduction or the Mitsunobu reaction, and cis-dihydroxylation in stereo- and regioselective manners.
- Kwon, Yong-Uk,Lee, Changgook,Chung, Sung-Kee
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p. 3327 - 3338
(2007/10/03)
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- Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using OsO4/TMEDA
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The oxidation of a range of cyclic allylic alcohols and amides with OsO4/TMEDA is presented. Under these conditions, hydrogen bonding control leads to the (contrasteric) formation of the syn isomer in almost every example that was examined. Evidence for the bidentate binding of TMEDA to OsO4 is presented and a plausible mechanism described.
- Donohoe, Timothy J.,Blades, Kevin,Moore, Peter R.,Waring, Michael J.,Winter, Jon J. G.,Helliwell, Madeleine,Newcombe, Nicholas J.,Stemp, Geoffrey
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p. 7946 - 7956
(2007/10/03)
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- Catalytic behaviour of chloroperoxidase from Caldariomyces fumago in the oxidation of cyclic conjugated dienes
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Chloroperoxidase from Caldariomyces fumago has been investigated as a catalyst for the oxidation of cyclic conjugated dienes. The nature of the substituents and the size of the carbocycle affect the enantioselectivity of the enzyme. An unexpected course o
- Sanfilippo, Claudia,Nicolosi, Giovanni
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p. 1889 - 1892
(2007/10/03)
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- Asymmetric induction of conduritols via AAA reactions: Synthesis of the aminocyclohexitol of hygromycin A
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Two synthetic routes towards the construction of the aminocyclohexitol moiety of hygromycin A have been developed based on palladium-catalyzed asymmetric alkylation of conduritol derivatives. A protocol has been established whereby this biologically relev
- Trost, Barry M.
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p. 1619 - 1629
(2007/10/03)
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- A New Convergent Route to Conduritols A-F from a Common Chiral Building Block
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(matrix presented) A diastereocontrolled route to conduritols A-F has been developed starting from a common chiral building block containing an oxabicyclo-[3.2.1]octane framework.
- Kadota, Kohei,Takeuchi, Miwako,Taniguchi, Takahiko,Ogasawara, Kunio
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p. 1769 - 1772
(2007/10/03)
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- Facile synthetic routes to all possible enantiomeric pairs of conduritol stereoisomers via efficient enzymatic resolution of conduritol B and C derivatives
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matrix presented The first synthesis of all possible enantiomeric pairs of conduritol stereoisomers has been accomplished by efficient enzymatic resolution of conduritol B and C derivatives, followed by oxidation/reduction and the Mitsunobu reaction in st
- Kwon, Yong-Uk,Chung, Sung-Kee
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p. 3013 - 3015
(2007/10/03)
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- A norbornyl route to cyclohexitols: Stereoselective synthesis of conduritol-E, allo-inositol, MK 7607 and gabosines
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A novel fragmentation sequence within the norbornane system, involving C1-C7 bond scission, provides convenient access to a highly functionalized and versatile cyclohexenoid building block which has been further elaborated to a range of cyclohexitols such as, conduritol E, allo-inositol and gabosine B. Our synthesis of the structure corresponding to gabosine K indicates that the structure of this natural product needs to be revised. (C) 2000 Elsevier Science Ltd.
- Mehta, Goverdhan,Lakshminath, Sripada
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p. 3509 - 3512
(2007/10/03)
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- Integrated synthesis of conduritols A-F using a single chiral building block
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Six possible diastereomers of conduritols have been synthesized diastereoselectively in an integrated manner starting from a single chiral precursor, which served as a synthetic equivalent of chiral cis-1,4-dihydroxycyclohexa-2,5-diene.
- Honzumi, Masatoshi,Hiroya, Kou,Taniguchi, Takahiko,Ogasawara, Kunio
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p. 1985 - 1986
(2007/10/03)
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- Practical synthesis of all inositol stereoisomers from myo-inositol
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Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis- inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.
- Chung, Sung-Kee,Kwon, Yong-Uk
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p. 2135 - 2140
(2007/10/03)
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- Efficient synthesis of (±)-, (+)-, and (-)-conduritol C via palladium(II)-catalyzed 1,4-diacetoxylation in combination with enzymatic hydrolysis
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Palladium-catalyzed diacetoxylation of 5,6-isopropylendioxy-1,3- cyclohexadiene (3) was stereoselective and gave the trans-diacetate 4 (> 94% trans), which after hydrolysis and deprotection, afforded (±)-conduritol. Enzymatic hydrolysis of diacetate 4 produced enantiomerically pure diol (-)- 5 (>99.5% ee) and enantiomerically pure (+)-4 (>99.5% ee). Compounds (-)-5 and (+)-4 were subsequently transformed to (-)- and (+)-conduritol C, respectively.
- Yoshizaki, Hiroki,Baeckvall, Jan-E.
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p. 9339 - 9341
(2007/10/03)
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- The directed dihydroxylation of allylic alcohols
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The preparation and dihydroxylation of a series of polyenes and cyclic allylic alcohols using the TMEDA/osmium tetroxide mixture is reported. Remarkably, these reagents lead to high levels of regiochemical and stereochemical control as the oxidant hydroge
- Donohoe, Timothy J.,Moore, Peter R.,Waring, Michael J.,Newcombe, Nicholas J.
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p. 5027 - 5030
(2007/10/03)
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- Enzymatic desymmetrisation of conduritol D. Preparation of homochiral intermediates for the synthesis of cyclitols and aminocyclitols
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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
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p. 2665 - 2670
(2007/10/03)
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- Stereoselctive Total Syntheses of Conduritols-F and -A from Tricyclo2,7>undeca-4,9-dien-3,6-dione
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Effective syntheses of conduritols-F and A have been accomplished starting from cyclopentadiene/benzoquinone adduct 6.Key intermediates are tricyclic acetates 9 and 15 which, when subjected to flash vacuum thermolysis, afford epoxycyclohexene diacetate 10 and cyclohexadiene diacetate 17, respectively.Conduritol-F is obtained from 10 by hydrolysis while conduritol-A is produced from 17 by osmylation.In both cases the final step involves removal of the acetate groups by amidation with ammonia.
- Mgani, Quintino A.,Klunder, Antonius J. H.,Nkunya, Mayunga H. H.,Zwanenburg, Binne
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p. 4661 - 4664
(2007/10/02)
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- Stereospecific synthesis of conduramine-F4 and conduritol-F (Leucanthemitol)
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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
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p. 2103 - 2108
(2007/10/02)
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- Synthesis of Conduritols A, (+)-C and (-)-C from D-Galactose
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A general approach for the stereoselective synthesis of conduritols A 1, (+)-C 3 and (-)-C 3 starting from D-galactose is described.The utility of the key cyclohexenone intermediate 11 leading to the synthesis of conduritols 1, (+)-3 and (-)-3 by straightforward synthetic manipulations is described.
- Mereyala, Hari Babu,Gaddam, Reddy
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p. 2187 - 2190
(2007/10/02)
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- Improved preparation of (±)-(1,3/2,4)-5-cyclohexene-1,2,3,4-tetrol [(±)-conduritol-B] and its reaction with hydrobromic and hydrochloric acid; synthesis and characterisation of some (±)-1-deoxy-1-halo- and (±)-1,4-dideoxy-1,4-dihalo-conduritols
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An active-site directed, covalent inhibitor of α-glucosidases is the mixture of (±)-1-bromo (1,3/2,4)-5-cyclohexene-2,3,4-triol [(±)-1-bromo-1-deoxyconduritol F] (2), formed on treatment of (±)-conduritol-B (3) with hydrogen bromide and termed 'bromo cond
- Guo,Haines,Pyke,Pyke,Taylor
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p. 147 - 153
(2007/10/02)
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- A novel synthesis of Conduritol-C and Conduritol-E via p-benzoquinone
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A new and sterospecific synthesis for Conduritol-C 8 and Conduritol-E 13a has been developed starting from p-benzoquinone 1. 1,4-oxygen functionalities were introduced in both synthesis by the reduction of dibromo p-benzoquinone 2 with NaBH4. 2
- Secen,Maras,Sutbeyaz,Balci
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p. 2613 - 2619
(2007/10/02)
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- Enantiospecific and Stereoselective Synthesis of (-)-Conduritol C from Chlorobenzene via Microbial Oxidation and Epoxidation
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A four-step route to (-)-conduritol C 1 is described, via the enantiospecific conversion of chlorobenzene to the diene cis-diol 7 and subsequent cis-epoxidation to yield 8.
- Carless, Howard A. J.
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p. 234 - 235
(2007/10/02)
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- Catalytic One-Pot Osmylation of Cyclohexadienes: Stereochemical and Conformational Studies of the Resulting Polyols
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Catalytic double osmylation is described for a series of cyclohexadienes in acetone/H2O in the presence of the co-oxidant N-methylmorpholine N-oxide (NMO).The formation of polyols occurred stereospecifically with cyclohexadienes 3, 7, and 11a, leading thereby to tetrols 5a, and 9a and to allo-inositol (14a), respectively.To the contrary, trans-cyclohexadiene-diol 15a gave a mixture of the stereoisomeric inositols 18a (epi), 19a (neo), and 20a (chiro).High-field NMR let to clearcut conformational analyses of the polyhydroxylated derivatives.
- Tschamber, Theophile,Backenstrass, Frederique,Fritz, Hans,Streith, Jacques
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p. 1052 - 1060
(2007/10/02)
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- A New and Stereospecific Synthesis of Conduritol-F and Conduritol-B
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A new and stereospecific synthesis for conduritol-F has been developed starting from trans-benzenediacetate 5 and oxepine-benzeneoxide 8 where the oxygen functionalities were introduced in both cases by photooxygenation; suitable ring opening reactions gave the desired conduritol-F.Acid-catalyzed ring opening reaction of 11 in acetic anhydride gave conduritol-F and conduritol-B in a ratio of 2:1.
- Secen, Hasan,Suetbeyaz, Yasar,Balci, Metin
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p. 1323 - 1326
(2007/10/02)
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- Total Syntheses of (-)-Conduritol B ((-)-1L-Cyclohex-5-ene-1,3/2,4-tetrol) and of (+)-Conduritol F ((+)-1D-Cyclohex-5-ene-1,2,4/3-tetrol). Determination of the Absolute Configuration of (+)-Leucanthemitol
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The 'naked sugar' (+)-(1R,2R,4R)-2-endo-cyano-7-oxabicyclohept-5-en-2-exo-yl acetate ((+)-4) was converted (7 steps , 45percent overall) with high stereoselectivity into (-)-(4R,5S,6R)-4,5,6-tris(oxy)cyclohex-2-en-1-one (
- Drian, Claude Le,Vionnet, Jean-Paul,Vogel, Pierre
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p. 161 - 168
(2007/10/02)
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- SHORT SYNTHESIS OF CONDURITOLS A AND D, AND DEHYDROCONDURITOLS, FROM BENZENE: THE PHOTO-OXIDATION OF cis-CYCLOHEXA-3,5-DIENE-1,2-DIOL
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Diene (1), available by microbial oxidation of benzene, undergoes reaction with singlet oxygen to yield endoperoxides (2) and (3); reduction or rearrangement of these compounds gives conduritols (5) and (6) or dehydroconduritols (8) and (9), respectively.
- Carless, Howard A. J.,Oak, Ozer Z.
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p. 1719 - 1720
(2007/10/02)
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- A Novel and Stereospecific Synthesis of Conduritol-A
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A new and stereospecific synthesis for conduritol-A has been developed starting from cyclohexa-1,4-diene where hydroxy groups have been introduced by classical KMnO4-oxidation followed by photo-oxygenation; suitable ring-opening reactions gave the desired
- Suetbeyaz, Yasar,Secen, Hasan,Balci, Metin
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p. 1330 - 1331
(2007/10/02)
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