137567-79-4Relevant academic research and scientific papers
Concise synthesis of (+)-conduritol F and inositol analogues from naturally available (+)-proto-quercitol and their glucosidase inhibitory activity
Worawalai, Wisuttaya,Rattanangkool, Eakkaphon,Vanitcha, Avassaya,Phuwapraisirisan, Preecha,Wacharasindhu, Sumrit
, p. 1538 - 1540 (2012/04/04)
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.
Toluene dioxygenase-mediated oxidation of dibromobenzenes. Absolute stereochemistry of new metabolites and synthesis of (-)-conduritol E
Finn, Kevin J.,Collins, Jonathan,Hudlicky, Tomas
, p. 7471 - 7476 (2007/10/03)
Dibromobenzenes (o-, m-, and p-isomers) were converted to the corresponding cis-cyclohexadiene diols by whole-cell fermentation with Escherichia coli JM 109 (pDTG601A), an organism over-expressing the enzyme toluene dioxygenase (TDO). Absolute stereochemi
Common-intermediate strategy for synthesis of conduritols and inositols via beta-hydroxy cyclohexenylsilanes.
Heo, Jung-Nyoung,Holson, Edward B,Roush, William R
, p. 1697 - 1700 (2007/10/03)
[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
Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using OsO4/TMEDA
Donohoe, Timothy J.,Blades, Kevin,Moore, Peter R.,Waring, Michael J.,Winter, Jon J. G.,Helliwell, Madeleine,Newcombe, Nicholas J.,Stemp, Geoffrey
, p. 7946 - 7956 (2007/10/03)
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.
Facile syntheses of all possible diastereomers of conduritol and various derivatives of inositol stereoisomers in high enantiopurity from myo-inositol
Kwon, Yong-Uk,Lee, Changgook,Chung, Sung-Kee
, p. 3327 - 3338 (2007/10/03)
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.
Catalytic behaviour of chloroperoxidase from Caldariomyces fumago in the oxidation of cyclic conjugated dienes
Sanfilippo, Claudia,Nicolosi, Giovanni
, p. 1889 - 1892 (2007/10/03)
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
Asymmetric induction of conduritols via AAA reactions: Synthesis of the aminocyclohexitol of hygromycin A
Trost, Barry M.
, p. 1619 - 1629 (2007/10/03)
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
Facile synthetic routes to all possible enantiomeric pairs of conduritol stereoisomers via efficient enzymatic resolution of conduritol B and C derivatives
Kwon, Yong-Uk,Chung, Sung-Kee
, p. 3013 - 3015 (2007/10/03)
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
A New Convergent Route to Conduritols A-F from a Common Chiral Building Block
Kadota, Kohei,Takeuchi, Miwako,Taniguchi, Takahiko,Ogasawara, Kunio
, p. 1769 - 1772 (2007/10/03)
(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.
A norbornyl route to cyclohexitols: Stereoselective synthesis of conduritol-E, allo-inositol, MK 7607 and gabosines
Mehta, Goverdhan,Lakshminath, Sripada
, p. 3509 - 3512 (2007/10/03)
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.
