Tetrahedron

Lignanes. 15. Première Synthèse Totale de la (−)-α-Conidendrine Naturelle

P Boissin, R Dhal, E Brown

Index: Boissin, Partrick; Dhal, Robert; Brown, Eric Tetrahedron, 1992 ,  vol. 48,  # 4  p. 687 - 694

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Citation Number: 11

Abstract

Abstract (−)-α-Conidendrin 1 was synthesized according to a general reactionscheme that could be applied to other retrolignans as well. Thus, treatment of the optically active β-benzyl- γ-butyrolactone (R)-(+)-4 with NBS, followed with benzyl alcohol, selectively introduced a benzyloxy group in the benzylic position and afforded the mixture of epimers 7. α-Alkylation of the lithium enolate of the corresponding silyl ethers 10, with O-benzylvanillyl bromide ...