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. 1998 Nov 16;37(21):2995-2998.
doi: 10.1002/(SICI)1521-3773(19981116)37:21<2995::AID-ANIE2995>3.0.CO;2-6.

Total Synthesis of Himastatin: Confirmation of the Revised Stereostructure

Theodore M Kamenecka  1 , Samuel J Danishefsky  1
Affiliations

Total Synthesis of Himastatin: Confirmation of the Revised Stereostructure

Theodore M Kamenecka et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: Alkaloids; Antibiotics; Himastatin; Total synthesis.

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