化学
烯丙基重排
三氟化硼
二醇
烯类反应
双键
四氢呋喃
药物化学
戒指(化学)
桦木还原
质谱
立体化学
有机化学
催化作用
离子
溶剂
作者
I. G. Guest,John G. Jones,B. A. Marples,Matthew J. Harrington
出处
期刊:Journal of the Chemical Society. C.Organic
[The Royal Society of Chemistry]
日期:1969-01-01
卷期号: (19): 2360-2367
被引量:4
摘要
Reaction of three 3β-hydroxy-derivatives of Westphalen's diol with lead tetra-acetate is described. The major products are the ethers 6β-acetoxy-3β,5-oxaethano-19-nor-5β-cholest-9(10)-ene (VIa), 6β-acetoxy-16,16-dibenzyl-3β,5-oxaethano-19-nor-5β-androst-9(10)-17-one (VIb), and 6β-fluoro-3β,5-oxaethano-19-nor-5β-androst-9(10)-en-17-one (VIc) in which the original 5β-methyl group has been functionalised. Oxidation of (VIa) with chromic acid gave products of attack at the 9,10-double bond and/or the allylic position 11. The reduction of (VIa) and subsequent oxidation and boron trifluoride-catalysed cleavage of the tetrahydrofuran ring is described. The configurations of certain compounds were determined from 1H n.mr. spectra data and the mass spectra of some compounds are briefly discussed.
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