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Carbohydrate‐Based Studies Toward the Synthesis of Hamigeromycin E: A Stereoselective Total Synthesis of an Isomer of Zeaenol
Author(s) -
Saidachary Gannerla,
China Raju Bhimapaka
Publication year - 2016
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201500267
Subject(s) - chemistry , stereoselectivity , ring closing metathesis , mitsunobu reaction , total synthesis , formylation , metathesis , stereochemistry , salt metathesis reaction , carbohydrate , combinatorial chemistry , organic chemistry , catalysis , polymerization , polymer
A stereoselective synthesis of 14‐membered macrolide hamigeromycin E ( 6 ) has been studied by employing ortho ‐lithiated formylation, Barbier allylation, Julia – Kocienski olefination, Mitsunobu esterification, and ring‐closing metathesis ( RCM ) reactions. The final RCM reaction did not provide the target molecule. This study has prompted us to synthesize a stereoisomer of zeaenol and accomplish the total synthesis with the above protocols.