Journal of Organic Chemistry p. 2932 - 2939 (1986)
Update date:2022-08-17
Topics:
Kametani, Tetsuji
Tsubuki, Masayoshi
Higurashi, Katsuyuki
Honda, Toshio
The synthesis of 2-deoxycrustecdysone has been accomplished from pregnenolone.The key reaction is based on succesful stereochemical control at C-20 and C-22 involving the stereoselective reduction of lactone 23, derived from 20-oxosteroid 20 and 2-lithiofuran, to give γ-butyrolactone 25 having a(20R,22R)-20,22-diol functionality. 5-Epi-2-deoxymakisterone A, 5,24-epi-2-deoxymakisterone A, and 24-epi-2-deoxymakisterone A were also synthesized by application of the same sequence.
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