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Overview

The first stereo-controlled total syntheses of ieodomycins A and B have been accomplished in 15 steps using the chiral pool approach starting from D-glucose.The key features of this synthetic strategy are Wittig olefination, indium catalyzed Barbier reaction, and Martin sulfurane catalyzed dehydration to achieve preferential formation of the desired E isomer.

01 Jun 2011·Tetrahedron Letters

Stereo-conserved synthesis of syn-diarylheptanoids, active principles of Zingiber, starting from d-glucose

Author: Prasad, Uppuleti Viplava ; Bhosale, Sandeep ; Bhuniya, Debnath ; Vyavahare, Vinod P. ; Palle, Venkata P.

A highly efficient and stereo-controlled synthetic strategy has been developed to access syn-diarylheptanoids starting from D-glucose as a chiral pool.The 3-(R), 5-(S)-syn-diol stereochem. present in these heptanoids was obtained after conserving C2 and C4 stereochem. of D-glucose during the course of synthetic transformation.The key features of this synthetic strategy include: (i) conversion of D-glucose to a known chiral template armored with the required 1,3-syn-diol stereochem. as well as two terminal aldehyde functionalities for building up customized diaryl wings'; (ii) conversion of the known chiral template to a hemiacetal via an initial Wittig olefination at the C5-aldehyde; (iii) use of the hemiacetal as a common intermediate to obtain the individual heptanoids via a second Wittig reaction at its anomeric center using appropriately chosen ylides.

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