Studies in Steroid Total Synthesis. I. Resolution of a Bicyclic Intermediate

AJ Speziale, JA Stephens…

Index: Speziale et al. Journal of the American Chemical Society, 1954 , vol. 76, p. 5011

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Citation Number: 15

Abstract

A method for converting Woodward's dl-t~ ans-1, 4-diketo-2-methoxy-lO-methyl-A*~~- hexahydronaphthalene(I) into the optically pure enantiomorphs of t~ ans-2-keto-lO-methyl- A~~~-hexahydronaphthalene(IV) in 55-60;, over-all yield is described. Stereo-selective reduction of I yielded the monohydric alcohol IIa which was resolved vza its d-camphor-10- sulfonate esters. The pure diastereoisomers were reductively cleaved to (+)-and (-) IIc and ...