Syntheses via vinyl sulfones. 11. A triply convergent total synthesis of L-(-)-prostaglandin E2

RE Donaldson, JC Saddler, S Byrn…

Index: Donaldson, R. E.; Saddler, J. C.; Byrn, S.; McKenzie, A. T.; Fuchs, P. L. Journal of Organic Chemistry, 1983 , vol. 48, # 13 p. 2167 - 2188

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Citation Number: 110

Abstract

(6) The chiral 15-(S)-trans-~ inyl iodide precursor (prostaglandin numbering) to organolithium reagent 7b is available either by classical resolution of the tram-halovinyl alcohol [AF Kluge, KG Untch, and JH Fried, J. Am. Chem. SOC., 94, 7827 (1972)] or, more recently, by enantioselective reduction of the trans iodo vinyl ketone with a chiral hydride reducing reagent [R. Noyori, I. Tomino, and M. Nishizawa, ibid., 101, 5843 (1979) l.