On the optical activity of the 3-aryl-4-hydroxycoumarin isolated from Millettia griffoniana: molecular modelling and total synthesis

S Combes, JP Finet, D Siri

Index: Combes; Finet; Siri Journal of the Chemical Society. Perkin Transactions 1, 2002 , vol. 2, # 1 p. 38 - 44

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Citation Number: 27

Abstract

Semi-empirical calculations on 4-hydroxy-3-(3′, 4′-methylenedioxyphenyl)-5, 6, 7- trimethoxycoumarin, a natural product recently isolated from Millettia griffoniana, show low rotational barriers for the C (3)–C (1′) bond (19.9 kJ mol− 1) and for the inversion of the out- of-plane central 6-methoxy group (9.7 kJ mol− 1). The structure of this compound is confirmed by its synthesis in 4 steps from 3, 4, 5-trimethoxyphenol in 37% overall yield, the ...

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