Synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanone

G Solladié, N Gehrold, J Maignan

Index: Solladie, Guy; Gehrold, Nicolai; Maignan, Jean Tetrahedron Asymmetry, 1999 , vol. 10, # 14 p. 2739 - 2747

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Citation Number: 22

Abstract

The synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanone is described. A new chromylation method of β-ketosulfoxide 9 leading to the Michael acceptor 12 has been developed. Dilithium tetrachlorocuprate was shown to be a very efficient catalyst for the conjugate addition reaction of phenyl magnesium bromide to the α, β- unsaturated sulfoxide 12. The instability of the obtained adducts 10 represents a limitation ...