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Stereoselective Approach towards the Synthesis of 3 R , 5 S Gingerdiol and 3 S , 5 S Gingerdiol
Author(s) -
Markad Sachin B.,
Bhosale Viraj A.,
Bokale Suvarna R.,
Waghmode Suresh B.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201803154
Subject(s) - stereoselectivity , heptanal , wittig reaction , aldehyde , proline , chemistry , adduct , stereochemistry , organic chemistry , catalysis , amino acid , biochemistry
Abstract An operationally simple and concise stereoselective synthesis of both natural 3 R , 5 S gingerdiol and 3 S , 5 S gingerdiol has been achieved from achiral n ‐heptanal by employing iterative proline catalysed α‐aminoxylation, followed by Horner−Wadsworth−Emmons or Wittig olefination reactions as key steps. The adducts formed in high enantiopurity as well as syn or anti ‐1,3‐diols units were synthesized with excellent diastereoselectivity from γ‐hydroxy aldehyde by using D or L‐ proline.