Asymmetric Synthesis of Chiral Flavan-3-Ols

Abstract

Flavan-3-ols are a series of natural products widely present in plants and show versatile biological activities. The structures of such compounds are characterized by owing two adjacent chiral centers and three rings. Their interesting structures and promising biological activities have driven increasing research developments toward the preparation of enantioenriched flavan-3-ols. This review summarizes the recent approaches for the asymmetric synthesis of chiral flavan-3-ols from two strategies in the construction of chiral centers. The key steps in the synthetic protocol involve Sharpless asymmetric dihydroxylation, Shi asymmetric epoxidation and Sharpless asymmetric epoxidation.

Keywords:

• Flavan-3-ols
• Asymmetric synthesis
• Sharpless asymmetric dihydroxylation
• Shi asymmetric epoxidation
• Sharpless asymmetric epoxidation

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was supported by the Ph.D. startup fund of the University of South China (Grant No. 2015XQD25); the undergraduate research learning and innovative experiment project (Grant No. 2017XJYZ043); the young and middle-aged innovative personnel training project of the Hunan Province Cooperative Innovation Center for Molecular Target New Drug Study (Grant No. 0223-0002-00013 and 0223-0002-000200-52); the Key Project of Hunan Province Science and Technology Department (Grant No. 2016DK2001); the Key Project of Hengyang Science and Technology Department (No. 2017KJ166); the innovative and entrepreneurial talent of Hengyang (Grant No. 2017-1); the Natural Science Foundation of Hunan Province (Grant No. 2018JJ3426).