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通过 Prins [3 + 2] 策略实现对格雷烷二萜类化合物 mollanol A 的全合成。

Toward the total synthesis of grayanane diterpene mollanol A by a Prins [3 + 2] strategy.

机构信息

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng District, Beijing 100050, China.

出版信息

Org Biomol Chem. 2020 Mar 14;18(10):1877-1880. doi: 10.1039/d0ob00160k. Epub 2020 Feb 26.

Abstract

Toward the total synthesis of a novel grayanoid, mollanol A, we developed a concise convergent strategy based on a formal [3 + 2] cyclization initiated by the Prins reaction. In this key intermolecular reaction between an unprotected hydroxyaldehyde and activating-group-free olefins, two chiral carbons and one densely substituted tetrahydrofuran ring were constructed stereoselectively.

摘要

为了全合成新型格雷阿烷型倍半萜 mollanol A,我们开发了一种基于普林斯反应引发的形式[3+2]环化的简洁的汇聚策略。在这个非保护羟基醛和无活化基团的烯烃之间的关键的分子间反应中,两个手性碳原子和一个密集取代的四氢呋喃环被立体选择性地构建。

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