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The Spongistatins: Architecturally Complex Natural Products—Part Two: Synthesis of the C(29–51) Subunit, Fragment Assembly, and Final Elaboration to (+)‐Spongistatin 2
Author(s) -
Smith III Amos B.,
Lin Qiyan,
Doughty Victoria A.,
Zhuang Linghang,
McBriar Mark D.,
Kerns Jeffrey K.,
Brook Christopher S.,
Murase Noriaki,
Nakayama Kiyoshi
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<196::aid-anie196>3.0.co;2-t
Subject(s) - elaboration , fragment (logic) , stereochemistry , protein subunit , epimer , chemistry , total synthesis , computer science , biochemistry , programming language , philosophy , humanities , gene
An advanced ABCD fragment (see picture) constructed on the way to the total synthesis of the potent antitumor agent (+)‐spongistatin 2 has also been used in a formal total synthesis of (+)‐spongistatin 1. In both cases the critical step was an acid‐mediated epimerization in the presence of Ca 2+ ions to stabilize the axial–equitorial CD spiroketal.