Synthesis 1995; 1995(2): 199-206
DOI: 10.1055/s-1995-3870
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

A Synthesis of Jaspamide Based on 1,2-Metallate Rearrangements of α-Heteroalkenylmetal Derivatives

Philip Ashworth, Brian Broadbelt, Pawel Jankowski, Philip Kocienski* , Austen Pimm, Richard Bell
  • *Department of Chemistry, The University, Southampton, SO17 1BJ, UK
Further Information

Publication History

Publication Date:
31 December 2000 (online)

Jaspamide (Jasplakinolide), a marine cyclodepsipeptide, was synthesised from tripeptide fragment 4 and (2S,4E,6R,8S)-8-benzoyloxy-2,4,6-trimethylnon-4-enoic acid (3). The tripeptide fragment was prepared from β-tyrosine derivative 6, Boc-2-bromoabrine (8), and alanine. β-Tyrosine derivative 6 was prepared by asymmetric conjugate amination of methyl p-hydroxycinnamate. Bromabrine derivative 8 was prepared from tryptophan. Key steps in the synthesis of the polyketide fragment 3 include 1,2-metallate rearrangement of a metallated dihydropyran and a metallated enol carbamate derivative.