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Asymmetric Total Synthesis of Rhizoxin D
Author(s) -
Keck Gary E.,
Wager Carrie A.,
Wager Travis T.,
Savin Kenneth A.,
Covel Jonathan A.,
McLaws Mark D.,
Krishnamurthy Dhileep,
Cee Victor J.
Publication year - 2001
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(20010105)40:1<231::aid-anie231>3.0.co;2-w
Subject(s) - retrosynthetic analysis , aldol reaction , acetal , ketone , chemistry , stereochemistry , enantioselective synthesis , stannane , fragment (logic) , total synthesis , combinatorial chemistry , catalysis , computer science , organic chemistry , algorithm
Catalytic asymmetric allylation (CAA) using tributyl‐(2‐ethylallyl)stannane as a methyl ethyl ketone equivalent plays a key role in this synthesis of rhizoxin D. A subsequent substrate‐directed acetal aldol reaction, fragment assembly by a modified Julia procedure, and directed electron transfer reduction are used to complete the synthesis (see scheme).