(-)-Vinigrol 的可扩展全合成。

Scalable Total Synthesis of (-)-Vinigrol.

机构信息

Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.

Peking-Tsinghua Center for Life Sciences, Academy for Advanced Interdisciplinary Studies , Peking University , Beijing 100871 , China.

出版信息

J Am Chem Soc. 2019 Feb 27;141(8):3440-3443. doi: 10.1021/jacs.9b00621. Epub 2019 Feb 18.

DOI:10.1021/jacs.9b00621

PMID:30767520

Abstract

Vinigrol is a structurally and stereochemically complex natural product that displays various potent pharmacological activities, including the capability to modulate TNF-α. A new and efficient synthetic route toward this natural product has been developed to complete the asymmetric synthesis of (-)-vinigrol and provide over 600 mg of material, manifesting the power of macrocyclic stereocontrol and transannular Diels-Alder reaction.

摘要

威尼醇是一种结构和立体化学复杂的天然产物，具有多种有效的药理活性，包括调节 TNF-α 的能力。已经开发出一种新的、有效的合成途径来完成(-)-威尼醇的不对称合成，并提供了超过 600 毫克的产物，体现了大环立体控制和环间 Diels-Alder 反应的威力。