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Synlett 1989; 1989(1): 22-23
DOI: 10.1055/s-1989-34684
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Synthesis of Functionalized Prostaglandins via the Organozinc-Aided Three-Component Method

M. Suzuki* , H. Koyano, Y. Morita, R. Noyori
  • *Department of Chemistry, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publikationsdatum:
26. Februar 2002 (online)

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Michael reaction of (R)-4-(tert-butyldimethylsiloxy)-2-cyclopenten-1-one (1) with the organometallic reagent formed from dimethylzine and (S)-3-(tert-butyldimethylsiloxy)-1-lithio-1-octene (4) gives enolate 2, which is trapped with a variety of electrophiles (two aldehydes, a 2-nitro-l-alkene, and a propargyl iodide) in a regio- and stereocontrolled manner. This tandem sequence constitutes a convenient organornetallic route to physiologically significant prostaglandin analogues.