Premium
Revision of the Absolute Configuration of Salicylihalamide A through Asymmetric Total Synthesis
Author(s) -
Wu Yusheng,
Esser Lothar,
De Brabander Jef K.
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20001201)39:23<4308::aid-anie4308>3.0.co;2-4
Subject(s) - absolute configuration , total synthesis , metathesis , metabolite , stereochemistry , ring (chemistry) , chemistry , ring closing metathesis , organic chemistry , biochemistry , polymerization , polymer
A highly E ‐selective ring‐closing metathesis is the key to building the macrocyclic salicylate core of (+)‐salicylihalamide A ( 1 ). The synthesis results in a reassignment of the absolute configuration of natural (−)‐salicylihalamide A ( 2 ), a structurally unprecedented antitumor metabolite with a potentially novel mode of action.