Synthesis of 9,11-Secosteroids Pinnisterol E, Glaciasterol B, and 6-Keto-aplidiasterol B,Organic Letters

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Synthesis of 9,11-Secosteroids Pinnisterol E, Glaciasterol B, and 6-Keto-aplidiasterol B
Organic Letters ( IF 4.9 ) Pub Date : 2022-02-23 , DOI: 10.1021/acs.orglett.2c00281
Yinlong Miao ₁ , Xinghui Li ₂ , Mengqing Zhang ₁ , Huafang Fan ₁ , Jinghan Gui ₂

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A 10-step gram-scale synthesis of 9,11-secosteroid pinnisterol E from the inexpensive ergosterol is reported. This synthesis features a series of highly selective redox transformations such as regioselective olefin hydrogenation (PtO₂), acid-sensitive endoperoxide reduction (Al–Ni alloy, Zn), and regio- and diastereoselective dienone oxidation. The robustness of this strategy is clearly demonstrated through the formal synthesis of 11(9 → 7)abeo-steroid pleurocin B and the divergent synthesis of 9,11-secosteroids glaciasterol B and 6-keto-aplidiasterol B from the inexpensive cholesterol.

中文翻译：

9,11-Secosterols Pinnisterol E、Glaciasterol B 和 6-Keto-aplidiasterol B 的合成

报道了从廉价的麦角甾醇合成 9,11-secosteroid pinnisterol E 的 10 步克级合成。该合成具有一系列高度选择性的氧化还原转化，例如区域选择性烯烃氢化 (PtO ₂ )、酸敏感性内过氧化物还原 (Al-Ni 合金、Zn) 以及区域选择性和非对映选择性二烯酮氧化。该策略的稳健性通过 11(9 → 7) abeo -steroid pleurocin B 的正式合成和从廉价胆固醇不同合成 9,11-secosterol glaciasterol B 和 6-keto-aplidiasterol B 清楚地证明。

更新日期：2022-02-23

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