The stereochemistry of hydrogen elimination from C-7 during biosynthesis of ecdysones in insects and plants

昆虫和植物蜕皮激素生物合成过程中C-7位氢消除的立体化学

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Abstract

1. [7alpha-(3)H(1)]- and [7beta-(3)H(1)]-Cholesterol were synthesized by a modified method. 2. The stereochemistry of Delta(7)-bond formation during ecdysone and ecdysterone biosynthesis in the insect, Calliphora erythrocephala and the plants, Taxus baccata and Polypodium vulgare was investigated by using [4-(14)C,7alpha-(3)H(1)]cholesterol and [4-(14)C,7beta-(3)H(1)]cholesterol. 3. In each case, the 7beta hydrogen was stereospecifically eliminated. 4. The possible significance of the results is discussed in relation to double-bond formation in other systems and the stage at which the Delta(7) bond is introduced during ecdysone biosynthesis.

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