在假白榴脂酸A合成中关键中间体10-乙酰基-7-(叔丁基二苯基硅氧基甲基)-4-甲基双环[5.3.0]癸-4-烯-1-醇的合成
Synthesis of a key intermediate, 10-acetyl-7-(t-butyldiphenylsilyloxymethyl)-4-methylbicyclo[5.3.0]dec-4-en-1-ol, in the synthesis of pseudolaric acid A.
作者信息
Nakashima Katsuyuki, Kikuchi Naoki, Takehara Tasuku, Shiozawa Takayuki, Takaoka Shigeru, Tori Motoo
机构信息
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
出版信息
Nat Prod Commun. 2013 Jul;8(7):877-81.
PMID:23980415
Abstract
10-Acetyl-7-(t-butyldiphenylsilyloxymethyl)-4-methylbicyclo[5.3.0]dec-4-en-1-ol was synthesized by aldol cyclization to a five-membered ring, epoxidation, samarium diiodide-induced ring opening, and the RCM reaction to the seven-membered carbocycle. This method has succeeded in constructing the desired stereochemistry in the synthesis of pseudolaric acid A.
摘要
通过羟醛缩合环化形成五元环、环氧化、二碘化钐引发的开环以及向七元碳环的关环复分解反应合成了10-乙酰基-7-（叔丁基二苯基硅氧基甲基）-4-甲基双环[5.3.0]癸-4-烯-1-醇。该方法在合成伪土荆皮酸A中成功构建了所需的立体化学结构。
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