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Total Synthesis of the Callipeltoside Aglycon
Author(s) -
Paterson Ian,
Davies Robert D. M.,
Marquez Rodolfo
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(20010202)40:3<603::aid-anie603>3.0.co;2-o
Subject(s) - sonogashira coupling , aldol reaction , stereochemistry , tandem , chemistry , total synthesis , combinatorial chemistry , organic chemistry , palladium , catalysis , materials science , composite material
Following macrolactonization , a Sonogashira coupling leads efficiently from 1 and 2 to the aglycon of the structurally unique cytotoxic macrolide callipeltoside A, isolated in tiny quantities from the lithistid sponge Callipelta sp. Key steps in the preparation of macrolide precursor 1 include a boron‐mediated anti‐aldol coupling (A) in tandem with Yamamoto's vinylogous aldol reaction (B). TES=triethylsilyl.