Synthesis of Cardiotonic Steroids Oleandrigenin and Rhodexin B,The Journal of Organic Chemistry

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Synthesis of Cardiotonic Steroids Oleandrigenin and Rhodexin B
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-07-13 , DOI: 10.1021/acs.joc.1c00985
Zachary Fejedelem ₁ , Nolan Carney ₁ , Pavel Nagorny ₁

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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).

中文翻译：

强心类固醇夹竹桃苷元和罗得辛 B 的合成

本文描述了强心类固醇夹竹桃素 ( 7 ) 的简明合成，以及随后从容易获得的中间体 ( 8 ) 到天然产物罗得辛 B ( 2 ) 的精制，该中间体可通过三步从市售类固醇睾酮或 DHEA 衍生而来序列。这些研究的特点是基于 β14-羟基定向环氧化和随后的环氧化物重排，方便地安装 β16-氧化。随后 C17 呋喃部分的单线态氧氧化可通过 12 个步骤 (LLS)获得夹竹桃素 ( 7 )，并且8 的总产率为 3.1% 。使用 Pd(II) 催化剂，合成的夹竹桃素 ( 7 ) 成功地与基于L -吡喃鼠李糖苷的供体28进行糖基化，随后在酸性条件下脱保护，以 66% 的产率（两步）提供了细胞毒性天然产物罗糊精 B ( 2 ) ）。

更新日期：2021-08-07

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