Synlett 1989; 1989(1): 22-23
DOI: 10.1055/s-1989-34684
© 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.

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
Further Information

Publication History

Publication Date:
26 February 2002 (online)

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.