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Synlett 1992; 1992(6): 537-538
DOI: 10.1055/s-1992-21408
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Stereoselective Synthesis of the Cytotoxic Acetogenins (+)- and (-)-Muricatacin

James A. Marshall* , Gregory S. Welmaker
  • *Department of Chemistry and Biochemistry, The University of South Carolina, Columbia, South Carolina 29208, USA
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Publication Date:
08 March 2002 (online)

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Reduction of 2-tridecenoyl(tributyl)stannane (2) with (S)- or (R)-BINAL-H [lithium (1,1′-binaphthalene-2,2′-diolato)-(ethanolato)hydridoaluminate] followed by silylation and 1,3-isomerization afforded the γ-silyloxy allylstannanes (R)-5 and (S)-5, respectively, of ca. 95% ee. The former yielded the hydroxy ester (S,S)-8 of 95% ee upon addition to ethyl 3-formyl-2-propenoate (7) in the presence of diethyl ether-boron trifluoride complex. The enantiomer (R,R)-8 was likewise secured from 7 and (S)-5. Hydrogenation then tert-butyldimethylsilyl cleavage with hydrogen fluoride led directly to (+)-muricatacin (S,S-11) [(S,S)-5-hydroxy-4-heptadecanolide] from (S,S)-8 and (-)-muricatacin (R,R-11) from (R,R)-8.