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Total Synthesis of Himastatin: Confirmation of the Revised Stereostructure
Author(s) -
Kamenecka Theodore M.,
Danishefsky Samuel J.
Publication year - 1998
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/(sici)1521-3773(19981116)37:21<2995::aid-anie2995>3.0.co;2-6
Subject(s) - stille reaction , natural product , depsipeptide , stereochemistry , total synthesis , chemistry , stereoselectivity , organic chemistry , catalysis
A stereoisomer of the natural product and not himastatin, an unusual dimeric depsipeptide with promising antibiotic and antitumor properties, was obtained from pyrroloindoline anti ‐ cis ‐ 1 . This result led to a revision of the proposed stereostructure. The new stereostructure was confirmed by the total synthesis, which involves stereoselective access to the pyrroloindoline syn ‐ cis ‐ 1 and the 5‐hydroxypiperazic acid subunit and features a Stille coupling for the formation of the central carbon–carbon bond.