Asymmetric synthesis of (-)-solanidine and (-)-tomatidenol.,Organic & Biomolecular Chemistry

当前位置： X-MOL 学术 › Org. Biomol. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Asymmetric synthesis of (-)-solanidine and (-)-tomatidenol.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-04-02 , DOI: 10.1039/d0ob00457j
Yun Wang ₁ , Guanxin Huang ₂ , Yong Shi ₃ , Wei-Sheng Tian ₃ , Chunlin Zhuang ₁ , Fen-Er Chen ₄

Affiliation

A concise asymmetric synthesis of two naturally occurring seco-type cholestane alkaloids (-)-solanidine and (-)-tomatidenol from (-)-diosgenin with a linear reaction sequence of 12 steps and 13 steps, respectively, is reported. The synthetic strategy includes the highly controlled establishment of highly functionalized octahydroindolizine ((-)-solanidine) and 1-oxa-6-azaspiro[4.5]decane ((-)-tomatidenol) cores with five stereocenters, respectively, from (-)-diosgenin, featuring two stereoselective cascade transformations including a modified cascade ring-switching process of furostan-26-acid to open the E-ring of (-)-diosgenin and a cascade azide reduction/intramolecular reductive amination to close the E- and F-rings of (-)-solanidine and (-)-tomatidenol. This work should enable further explorations of chemical and biological spaces based on solanidine, tomatidenol and related natural products.

中文翻译：

（-）-茄啶和（-）-番茄甾醇的不对称合成。

据报道，从（-）-薯s皂苷元中线性合成的两种山高胆固醇型胆甾烷生物碱（-）-茄碱和（-）-番茄甾醇的简明不对称合成反应的线性反应顺序分别为12步和13步。合成策略包括高度受控地从（-）-分别建立具有五个立体中心的高度官能化的八氢吲哚嗪（（-）-茄啶）和1-oxa-6-氮杂螺[4.5]癸烷（（-）-番茄甾醇）核。薯gen皂素，具有两个立体选择性的级联转化，包括改良的呋喃斯坦-26-酸级联环转换过程以打开（-）-薯-皂苷元的E环，以及叠氮化物还原/分子内还原胺化以关闭E-和F- （-）-茄啶和（-）-番茄甾醇的环。

更新日期：2020-04-02

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11