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First Stereoselective Total Synthesis and Biological Evaluation of Amphidinin B and Its Analogues
Author(s) -
Yadav Jhillu S.,
Reddy A. Srinivas,
Reddy Ch. Suresh,
Reddy Basi V. Subba,
Saddanapu Venkateshwarlu,
Addlagatta Anthony
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001205
Subject(s) - chemistry , stereoselectivity , epoxide , kinetic resolution , stereochemistry , double bond , total synthesis , alkylation , ring (chemistry) , sharpless epoxidation , enantioselective synthesis , organic chemistry , catalysis
A highly stereoselective first total synthesis of amphidinin B is described. The key steps involved in this synthesis are the generation of the exo ‐double bond in the C 1 –C 9 segment, the Barbier allylation, enzymatic kinetic resolution, and the construction of the C 10 –C 21 segment by Sharpless asymmetric epoxidation, base‐induced epoxide ring‐opening, radical cyclization, diastereoselective reduction of the exo ‐cyclic double bond, one‐pot allylation followed by debenzylation, Evans alkylation, and Yamaguchi esterification.