Three-component coupling synthesis of prostaglandins. A simplified, general procedure

Abstract In the presence of dimethylzinc, ( R)-tert -butyldimethylsiloxy-2-cyclopentenone can be linked with ( S,E )-1-lithio-3- tert -butyldimethylsiloxy-1-octene and methyl 7-1odo-5-heptynoate, giving a protected 5,6didehydroprostaglandin E 2 - Use of an ω side-chain aldehyde or nitroalkene in place of the propargylic iodide affords the C-7 and C-6 functionalized prostaglandins, respectively. This new protocol constitutes the simplest three-component method for the synthesis of various natural and unnatural prostaglandins.

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