Convenient method for the functionalization of the 4- and 6-positions of the androgen skeleton.

Convenient method for the functionalization of the 4- and 6-positions of the androgen skeleton.
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DOI:
10.1039/c2cc31973j
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发表时间:
2012-06-14
期刊:
Chemical communications (Cambridge, England)
影响因子:
--
通讯作者:
Davies HM
Davies HM
中科院分区:
其他
文献类型:
--
作者:
Morton D;Dick AR;Ghosh D;Davies HM

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报道了甾体乙烯基重氮化合物的制备和反应性,提供了一种方便的、耐受取代基的、化学和立体选择性的从共同前体进入4-和6-取代雄激素类似物的方法。在二铑催化下,OH插入发生在类胡萝卜素位点,产生4-取代类固醇,但在银催化下,OH插入发生在插烯位置,产生6-取代类固醇。
The preparation and reactivity of steroidal vinyldiazo compounds is reported, providing a convenient, substituent tolerant, chemo- and stereoselective entry into 4- and 6-substituted androgen analogues from a common precursor. Under dirhodium catalysis, O—H insertion occurs at the carbenoid site, leading to 4-substituted steroids, but under silver catalysis, O—H insertion occurs at the vinylogous position, leading to 6-substituted steroids.
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