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Enantioselective Total Synthesis of Avarol and Avarone
Author(s) -
Ling Taotao,
Xiang Alan X.,
Theodorakis Emmanuel A.
Publication year - 1999
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(19991018)38:20<3089::aid-anie3089>3.0.co;2-w
Subject(s) - total synthesis , enantioselective synthesis , cornerstone , stereochemistry , decarboxylation , quinone , antimitotic agent , chemistry , biology , organic chemistry , microbiology and biotechnology , visual arts , art , catalysis , microtubule , tubulin
Formation of the C11−C1′ bond through application of Barton's radical decarboxylation and quinone addition is the cornerstone of a new convergent and concise synthesis of the marine metabolites avarol ( 1 ) and avarone ( 2 ; see scheme), for which antimitotic, antileukemic, and antiviral effects have been reported.