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Communication | Special issue | Vol 28, No. 1, 1989, pp.59-62
Published online, 1st January, 1970
DOI: 10.3987/COM-88-S23
Stereocontrolled Synthesis of the Withanolide D Side Chain from 20-Oxosteroid

Tetsuji Kametani, Masayoshi Tsubuki, and Toshio Honda*

*Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


A new procedure for the construction of the withanolide D side chain starting from 20-oxopregnane is described. The key reactions are stereochemical control of C-20 and C-22 positions involving stereoselective hydrogenation of the enone 4, and an efficient transformation of the resulting γ-lactone 5 into the δ-lactone 8. Successful isomerization of the olefin 12 using RhCl3 is also reported.