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Synthesis 1995; 1995(8): 1007-1013
DOI: 10.1055/s-1995-4035
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A Synthesis of (3R*,4R*)-Luffariolide E via 1,2-Metallate Rearrangement

Georges Hareau-Vittini, Philip Kocienski* , Gillian Reid
  • *Department of Chemistry, The University, Southampton, SO17 1BJ, UK
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Publication Date:
31 December 2000 (online)

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A key step in the synthesis of (3R*,4R*)-Luffariolide E is a 1,2-metallate rearrangement of a higher order cuprate to generate a trisubstituted double bond stereoselectively. The synthetic product is a diastereoisomer of the natural marine cytotoxic agent (3S,4R)-Luffariolide E.

radical cyclisation - metallate rearrangement - organocuprate - trisubstituted alkene - marine cytotoxin - sesterterpenoid