Stereoselective synthesis of (.+-.)-11-hydroxy-trans-8-dodecenoic acid from 10-undecenoic acid

T Hirao, K Hayashi, Y Fujihara, Y Ohshiro…

Index: Hirao, Toshikazu; Hayashi, Ken-ichiro; Fujihara, Yoshimi; Ohshiro, Yoshiki; Agawa, Toshio Journal of Organic Chemistry, 1985 , vol. 50, # 2 p. 279 - 281

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Citation Number: 17

Abstract

Reductive deconjugation of 6 was accomplished by treatment with diethyl phosphonate and triethylamine and resulted in the stereoselective formation of the trans-@, y-unsaturated ketone 7 (77%) with no detectable production of the cis isomer or a,@-unsaturated ketone. This high selectivity is of the key features of the present approach. The ketone 7 was reduced to the alcohol 8 with Na13H4. Hyrolysis of the tert-butyl ester 8 with ...