Bulletin of the Chemical Society of Japan p. 2298 - 2303 (1993)
Update date:2022-08-02
Topics:
Kuroda, Chiaki
Shimizu, Shigeru
Haishima, Takahiro
Satoh, James Y.
Synthesis of 10-epi-frullanolide (3) is reported via the intramolecular cyclization of ω-formyl-α-trimethylsilylmethyl-α,β-unsaturated ester.The cyclization precursor, ethyl (Z)-5-(2-formyl-1,3-dimethyl-2-cyclohexenyl)-2-trimethylsilylmethyl-2-pentenoate (17), was prepared from 2,6-dimethyl-2-cyclohexen-1-one through the dialdehyde monoacetal as the key intermediate.Cyclization of 17 with tetrabutylammonium fluoride produced the hydroxy ester having C(6α)-H and C(7β)-H, which was hydrolyzed, then subjected to Fujisawa's lactonization to afford 3.
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