Total synthesis of the ethyl ester of the major urinary metabolite of prostaglandin E2

DF Taber, D Teng

Index: Taber, Douglass F.; Teng, Dawei Journal of Organic Chemistry, 2002 , vol. 67, # 5 p. 1607 - 1612

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Citation Number: 21

Abstract

The requisite dienal 5 was prepared by ozonolysis 8 of cyclohexene to give ethyl 6-oxohexanoate 11 (Scheme 2). Wittig reaction of the phosphonium salt with 1 mol equiv of KHMDS proceeded smoothly to give Z,E-dienol 12. 9 The geometry of the conjugated diene was assigned by comparison of the 13 C NMR of the C-5 and C-10 methylenes with similar compounds that we had previously prepared. 9 By comparing the C-5 and C-10 13 C chemical shifts of the dienol 12 (δ 63.7, ...