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Synlett 1995; 1995(9): 893-894
DOI: 10.1055/s-1995-5127
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A Synthesis of (3S*,4R*)-Luffariolide

G. Hareau-Vittini, P. J. Kocienski*
  • *Department of Chemistry, The University, Southampton, SO17 1BJ, U.K., Fax +44 (01703) 593781; E-mail pjk1@soton.ac.uk
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Publikationsdatum:
31. Dezember 2000 (online)

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A 1,2-metallate rearrangement of a higher order organocuprate was a key step in the synthesis of a trisubstituted alkene in the marine sesterterpenoid Luffariolide E. The synthesis shows that the stereochemistry of Luffariolides C, D, and E is (3S,4R).

sesterterpenoid - antitumour - radical cyclisation - 1,2-metallate rearrangement - higher order cuprate