Journal of the Chemical Society. Perkin transactions I p. 2049 - 2054 (1981)
Update date:2022-08-02
Topics:
Howard, Colin
Newton, Roger F.
Reynolds, Derek P.
Roberts, Stanley M.
Peracetic acid oxidation at -78 deg C of the dihydroxybicyclo<3.2.0>hepten-6-one (23) afforded the dihydroxylactone (24) which was protected as its bisdimethyl-t-butylsilyl ether (26) and reduced to the corresponding lactol (27).A Wittig reaction on (27), carried out in benzene with a short reaction time, gave mainly the required 11α-silyl ether (28) together with a trace of the 9α-silyl ether (29) which results from 1,5-migration of the silyl group.Oxidation of (28) followed by quantitative deprotection using aqueous HF in acetonitrile afforded (+/-)-PGE2 methyl ester (20).This short stereo- and regioselective total synthesis proceeds in an overall yield of 10percent starting from cyclopentadiene.
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