化学
双环分子
辛烷值
全合成
立体化学
分子内力
环加成
壬烷
天然产物
级联
螺旋桨烷
分子内反应
烯丙基重排
有机化学
催化作用
色谱法
作者
Jianhong Gao,P.V.D. Somasekhar Rao,Kaixiang Xu,Shuaifeng Wang,Yi Wu,Chi He,Hanfeng Ding
摘要
An asymmetric approach for the first total synthesis of (−)-rhodomollanol A, a highly oxidized diterpenoid, is described. The efficient synthetic strategy features three key transformations: (1) an oxidative dearomatization-induced (5 + 2) cycloaddition/pinacol-type 1,2-acyl migration cascade to build up the bicyclo[3.2.1]octane skeleton; (2) a retro-Dieckmann fragmentation/vinylogous Dieckmann cyclization cascade to assemble the bicyclo[3.3.0]octane subunit; and (3) a photo-Nazarov cyclization/intramolecular cycloetherification cascade to forge the 7-oxabicyclo[4.2.1]nonane core structure of the natural product.
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