Studies on flavans. 1. Facile synthesis of (+/-)-7-hydroxy-3',4'-methylenedioxyflavan and (+/-)-4'-hydroxy-7-methoxyflavan by a BF3.Et2O-mediated pyran cyclization

Y Li; J Yang; W Z Li; L Hou; J Xue; Y Li

doi:10.1021/np0001171

Studies on flavans. 1. Facile synthesis of (+/-)-7-hydroxy-3',4'-methylenedioxyflavan and (+/-)-4'-hydroxy-7-methoxyflavan by a BF3.Et2O-mediated pyran cyclization

J Nat Prod. 2001 Feb;64(2):214-6. doi: 10.1021/np0001171.

Authors

Y Li¹, J Yang, W Z Li, L Hou, J Xue, Y Li

Affiliation

¹ National Laboratory of Applied Organic Chemistry & Institute of Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, People's Republic of China. [email protected]

PMID: 11430003
DOI: 10.1021/np0001171

Abstract

A facile approach for the synthesis of flavans was developed by employing a BF3.Et2O-catalyzed pyran cyclization in an aprotic polar solvent as a key step, by which concise total syntheses of (+/-)-7-hydroxy-3',4'-methylenedioxyflavan (1) and (+/-)-4'-hydroxy-7-methoxyflavan (2), two naturally occurring flavans, were achieved.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Flavonoids / chemical synthesis*
Models, Chemical

Substances

4'-hydroxy-7-methoxyflavan
7-hydroxy-3',4'-(methylenedioxy)flavan
Flavonoids