Premium
The Spongistatins: Architecturally Complex Natural Products—Part One: A Formal Synthesis of (+)‐Spongistatin 1 by Construction of an Advanced ABCD Fragment
Author(s) -
Smith III Amos B.,
Doughty Victoria A.,
Lin Qiyan,
Zhuang Linghang,
McBriar Mark D.,
Boldi Armen M.,
Moser William H.,
Murase Noriaki,
Nakayama Kiyoshi,
Sobukawa Masao
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<191::aid-anie191>3.0.co;2-c
Subject(s) - stereochemistry , fragment (logic) , epimer , total synthesis , chemistry , computer science , programming language
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.