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Total Synthesis of the Marine Antibiotic Pestalone and its Surprisingly Facile Conversion into Pestalalactone and Pestalachloride A
Author(s) -
Slavov Nikolay,
Cvengroš Ján,
Neudörfl JörgMartin,
Schmalz HansGünther
Publication year - 2010
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.201003755
Subject(s) - surprise , natural product , total synthesis , metabolite , benzophenone , chemistry , antibiotics , intramolecular force , antifungal , combinatorial chemistry , organic chemistry , stereochemistry , microbiology and biotechnology , biology , biochemistry , psychology , social psychology
Surprise, surprise! The total synthesis of the marine natural product pestalone ( 1 ), a highly substituted benzophenone with strong antibiotic acitivity, has provided insight into the surprising tendency of this and related molecules to undergo intramolecular Cannizzaro–Tishchenko‐type reactions. Pestalone can be readily converted into pestalachloride A, a strongly antifungal metabolite isolated from an endophytic fungus, by simple treatment with ammonia at pH 8.