Two Novel Approaches toward Stereoselective Introduction of β-Hydroxymethyl Group at the C-7 Position of 5Androstene
摘要：
Two novel approaches to stereoselective introduction of 7β-hydroxymethyl group onto 5-androstene have been developed. In the first approach, coupling of benzyloxymethyl chloride with the 7-carbonyl group of 1 mediated by SmI2gives, after debenzylation, two isomers 4 and 5 respectively, which are stereoselectively deoxygenated by means of an ionic hydrogenation to afford 6. The second approach involves the addition of (isopropoxydimethylsilyl)methyl Grignard reagent (Tamao's reagent) to the 7-carbonyl group of 1, followed by oxidative cleavage of the silicon-carbon bond by hydrogen peroxide giving compound 5. Stereoselective deoxygenation of 5 via an ionic hydrogenation also affords 6. The relative configuration of 6 is confirmed by ROESY studies.
展开
DOI：
10.1055/s-2006-926356
被引量：
年份：
2006
相似文献
参考文献
引证文献
来源期刊
引用走势
辅助模式
引用
文献可以批量引用啦~
欢迎点我试用！
