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Synlett 1997; 1997(9): 1093-1095
DOI: 10.1055/s-1997-1547
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Synthesis of (+)-Homononactic Acid via Iodoetherification

Hiromasa Kiyota* , Masaki Abe, Yukie Ono, Takayuki Oritani
  • *Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku. Sendai 981, Japan. Fax +81-22-717-8783; e-mail kiyota@biochem.tohoku.ac.jp
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Publication Date:
31 December 2000 (online)

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(+)-Homononactic acid, one of the monomers of polynactin, and its 8-epimer were synthesized. The key step was cis-selective iodoetherification of the enone or the α-silyloxyolefin intermediates constructed with Wittig-Horner or Julia coupling reactions, respectively.

(+)-homononactic acid - tetranactin - iodoetherification - benzyl glycidyl ether - Julia reaction