Tetrahedron letters

Synthesis of (25R)-cholest-5-ene-3β, 26-diol and its radiolabeled analog

TE D'Ambra, NB Javitt, K Nakanishi, T Warchol

Index: D'Ambra, Thomas E.; Javitt, Norman B.; Nakanishi, Koji; Warchol, Tadeusz Tetrahedron Letters, 1997 , vol. 38, # 22 p. 3801 - 3804

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Citation Number: 10

Abstract

A new, convenient and stereoselective route to the synthesis of (25R)-cholest-5-ene-3β, 26- diol (1) and its radiolabeled analog 4 is described. The key step is a Julia condensation of sulfone 6 with aldehyde 12 to furnish compound 13. Further reduction of the α- hydroxysulfone moiety afforded 22, 23-unsaturated i-steroid 14. The double was reduced by hydrogen and by tritium to provide substrates for the preparation of 1 and 4, respectively.

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