产量(工程)
部分
环氧化物
化学
呋喃
天然产物
单线态氧
类固醇
组合化学
立体化学
催化作用
氧气
有机化学
生物化学
材料科学
冶金
激素
作者
Zachary Fejedelem,Nolan Carney,Pavel Nagorny
标识
DOI:10.1021/acs.joc.1c00985
摘要
This article describes a concise synthesis of cardiotonic steroids oleandrigenin (7) and its subsequent elaboration into the natural product rhodexin B (2) from the readily available intermediate (8) that could be derived from the commercially available steroids testosterone or DHEA via three-step sequences. These studies feature an expedient installation of the β16-oxidation based on β14-hydroxyl-directed epoxidation and subsequent epoxide rearrangement. The following singlet oxygen oxidation of the C17 furan moiety provides access to oleandrigenin (7) in 12 steps (LLS) and a 3.1% overall yield from 8. The synthetic oleandrigenin (7) was successfully glycosylated with l-rhamnopyranoside-based donor 28 using a Pd(II)-catalyst, and the subsequent deprotection under acidic conditions provided cytotoxic natural product rhodexin B (2) in a 66% yield (two steps).
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