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Total Synthesis of Macrolactin A with Versatile Catalytic, Enantioselective Dienolate Aldol Addition Reactions
Author(s) -
Kim Yuntae,
Singer Robert A.,
Carreira Erick M.
Publication year - 1998
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/(sici)1521-3773(19980518)37:9<1261::aid-anie1261>3.0.co;2-2
Subject(s) - total synthesis , enantioselective synthesis , aldol reaction , yield (engineering) , catalysis , stereochemistry , combinatorial chemistry , chemistry , sequence (biology) , organic chemistry , biochemistry , physics , thermodynamics
A highly convergent total synthesis of macrolactin A ( 1 ) utilizes modern asymmetric catalytic C–C coupling methods. The longest linear sequence in the route is 16 steps with an average yield of 86% per step. This total synthesis is valuable, because 1 , which has been shown to possess activity against HIV, is not readily accessible from its natural source, a taxonomically unclassified deep‐sea bacterium.