351885-26-2Relevant articles and documents
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.
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
Stereoselctive Total Syntheses of Conduritols-F and -A from Tricyclo2,7>undeca-4,9-dien-3,6-dione
Mgani, Quintino A.,Klunder, Antonius J. H.,Nkunya, Mayunga H. H.,Zwanenburg, Binne
, p. 4661 - 4664 (2007/10/02)
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.