A chiron approach to aminocytitols by Petasis-Borono-Mannich reaction: formal synthesis of (+)-conduramine E and (-)-conduramine E.
A chiron approach to a stereoselective route for the synthesis of aminocytitols from carbohydrates is described. The formal synthesis of (+)-conduramine E and (-)-conduramine E was achieved by utilizing this strategy. The key features of the synthetic strategy include one-pot three-component Petasis-Borono-Mannich reaction to introduce the syn-β-amino alcohol functionality of conduramine E and ring-closing metathesis to construct its carbocyclic core. The present synthetic approach paves the way for stereoselective synthesis of several conduramines starting from carbohydrates.
Division of Medicinal and Process Chemistry, CSIR-Central Drug Research Institute, Lucknow 226 001, India.
Partha
P
Ghosal
Arun K
AK
Shaw
D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry; D003514:Cyclohexylamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D003511:Cyclohexanols; D003514:Cyclohexylamines; C545151:conduramine E