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新型17-氧代雄甾烷甾体D环取代异恶唑啉衍生物的合成

Synthesis of novel steroidal D-ring substituted isoxazoline derivatives of 17-oxoandrostanes.

作者信息

Banday Abid H, Singh Swarn, Alam M Sarwar, Reddy Doma M, Gupta B D, Sampath Kumar H M

机构信息

Synthetic Chemistry Division, Indian Institute of Integrative Medicine, Jammu Tawi, India.

出版信息

Steroids. 2008 Mar;73(3):370-4. doi: 10.1016/j.steroids.2007.10.014. Epub 2007 Nov 17.

DOI:10.1016/j.steroids.2007.10.014
PMID:18166206
Abstract

A facile synthesis of isoxazoline derivatives of 17-oxoandrostane at the side chain of D-ring is reported. The scheme involves the transformation of the starting dehydroepiandrosterone acetate (ketone) to the Knoevenegel product, reduction to the nitrile, and elimination to the carboxaldehyde. Cycloaddition of nitrileoxides across olefinic aldehyde intermediate led to the synthesis of novel side chain isoxazoline derivatives.

摘要

报道了一种在D环侧链上简便合成17-氧代雄甾烷异恶唑啉衍生物的方法。该方案包括将起始的醋酸脱氢表雄酮(酮)转化为克脑文盖尔产物,还原为腈,并消除得到羧醛。腈氧化物与烯醛中间体进行环加成反应,从而合成了新型的侧链异恶唑啉衍生物。

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