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Total Synthesis of Himastatin: Confirmation of the Revised Stereostructure
Theodore M Kamenecka1, Samuel J Danishefsky1
1Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, Box 106, New York, NY 10021 (USA), Fax: (+1) 212-772-8691.
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.
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