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Asymmetric, Stereocontrolled Total Synthesis of Paraherquamide A
Author(s) -
Williams Robert M.,
Cao Jeffrey,
Tsujishima Hidekazu
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(20000717)39:14<2540::aid-anie2540>3.0.co;2-r
Subject(s) - total synthesis , stereochemistry , enantioselective synthesis , chemistry , intramolecular force , sn2 reaction , anthelmintic , derivative (finance) , combinatorial chemistry , ivermectin , biology , organic chemistry , catalysis , zoology , ecology , financial economics , economics
Paraherquamide A (1), a potent anthelmintic agent , isolated from various Penicillium species with activity against ivermectin‐resistant intestinal parasites, has been synthesized. The synthesis of a key intermediate, the α ‐isoprenylated, β ‐substituted hydroxyproline derivative, exploited a highly diastereoselective intramolecular S N 2′ cyclization as a key step. This procedure is the first asymmetric, stereocontrolled, total synthesis of 1 .