The stereochemistry of hydrogen elimination from C-7 during biosynthesis of ecdysones in insects and plants.
The stereochemistry of hydrogen elimination from C-7 during biosynthesis of ecdysones in insects and plants.
复制标题
昆虫和植物蜕皮激素生物合成过程中 C-7 氢消除的立体化学。
作者：
I. F. Cook;J. Lloyd;H. Rees;T. Goodwin
1.用改进的方法合成了[7 α-（3）H（1）]-和[7 β-（3）H（1）]-胆固醇。2.用[4-（14）C，7 α-（3）H（1）]胆固醇和[4-（14）C，7 β-（3）H（1）]胆固醇研究了昆虫红头丽蝇（Calliphoraerythrocephala）和植物红豆杉（Taxusbaccata）和水龙骨（Polypodiumvulgare）蜕皮激素和蜕皮甾酮生物合成过程中δ（7）-键形成的立体化学。3.在每种情况下，7 β氢被立体特异性消除。4.结果的可能意义进行了讨论，在其他系统中的双键的形成和阶段，其中Delta（7）键在蜕皮激素的生物合成过程中引入。
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.