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Stereocontrolled Synthesis of the Withanolide D Side Chain from 20-Oxosteroid

1989; Elsevier BV; Volume: 28; Issue: 1 Linguagem: Inglês

10.3987/com-88-s23

1881-0942

Toshio Honda, Tetsuji Kametani, Masayoshi Tsubuki,

Steroid Chemistry and Biochemistry

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 y-lactone 5 into the 6-lactone 8. Successful