A new strategy for the preparation of 11-oxygenated steroids synthesis of (±)-adrenosterone
A new strategy for the preparation of 11-oxygenated steroids synthesis of (±)-adrenosterone
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DOI：
10.1016/s0040-4039(98)01526-3
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发表时间：
1998-09-24
影响因子：
1.8
通讯作者：
Kaufman, MD
中科院分区：
文献类型：
--
作者：
Grieco, PA;May, SA;Kaufman, MD
1-[（叔丁基二甲基甲硅烷基）氧基]-2-甲基-1，3-环己二烯（5）在高极性介质中与2-甲基环戊烯酮进行共轭1，4-加成，随后在5.0 M LiClO 4中用苯基硫代碳酸二烯酯10对所得甲硅烷基烯醇醚（4）进行烷基化。Et 2 O提供衬底2。将2暴露于TMSOTf/TMSOCH 2CH 2 OTMS得到四环双缩酮3，其在四个步骤中转化为（+/-）-肾上腺甾酮（1）。(C)1998爱思唯尔科技有限公司版权所有。
Conjugate 1,4-addition of 1-[(tert-butyldimethylsilyl)oxy]-2methyl-1,3-cyclohexadiene (5) to 2-methylcyclopentenone in highly polar media and subsequent alkylation of the resultant silyl enol ether (4) with phenylthiodienyl carbonate 10 in 5.0 M LiClO4. Et2O provides substrate 2. Exposure of 2 to TMSOTf/ TMSOCH2CH2OTMS affords tetracyclic bis-ketal 3, which is converted into (+/-)-adrenosterone (1) in four steps. (C) 1998 Elsevier Science Ltd. All rights reserved.