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Asymmetric Total Syntheses of Marine Cyclic Depsipeptide Halipeptins A–D

✍ Scribed by Shouyun Yu; Xianhua Pan; Dawei Ma

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
259 KB
Volume
12
Category
Article
ISSN
0947-6539

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✦ Synopsis

Abstract

Halipeptins A–D (1 a–d) are a family of natural cyclic depsipeptides isolated from marine sponges. Total syntheses of these four compounds are detailed in this report. The key elements in this synthesis include the elaboration of the polysubstituted decanoic acid parts by two asymmetric aldol reactions, assembly of the N‐methyl‐δ‐hydroxyisoleucine residue by using either aza‐Claisen rearrangement or methylation of aspartates as the key steps, and macrocyclization at the polysubstituted decanoic acid alanine site.

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