Premium
Gephyronic Acid, a Missing Link between Polyketide Inhibitors of Eukaryotic Protein Synthesis (Part II): Total Synthesis of Gephyronic Acid
Author(s) -
Anderl Timo,
Nicolas Lionel,
Münkemer Johanna,
Baro Angelika,
Sasse Florenz,
Steinmetz Heinrich,
Jansen Rolf,
Höfle Gerhard,
Taylor Richard E.,
Laschat Sabine
Publication year - 2011
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/anie.201005605
Subject(s) - polyketide , aldol reaction , aldehyde , stereochemistry , total synthesis , chemistry , biology , combinatorial chemistry , biochemistry , biosynthesis , enzyme , catalysis
19 steps in the longest linear sequence are required in the 27 step total synthesis of gephyronic acid. A key step is a diastereodifferentiating Mukaiyama aldol reaction of an aldehyde and an enolsilane (see picture, PG: protecting group). The strongly cytotoxic target compound is a structural relative of the polyketide tedanolide and was isolated from the myxobacterium Archangium gephyra.