A total synthesis of racemic avenaciolide

JL Herrmann, MH Berger…

Index: Herrmann,J.L. et al. Journal of the American Chemical Society, 1979 , vol. 101, # 6 p. 1544 - 1549

Full Text: HTML

Citation Number: 70

Abstract

Abstract: A stereospecific total synthesis of racemic avenaciolide (1) has been realized in 64% overall yield starting from 5-n-octyL2 (5H)-furanone (3). The salient features of this synthesis include stereospecific substitution of both the@ and (Y positions of 3 via a conjugate addition-halogenation sequence. and transformation of an tu-methyl-tu- thiomethylbutyrolactone into an cu-methylene butyrolactone. The anion derived from ethyl ...

Related Articles:

Study on the reactivity of the alkyne component in ruthenium-catalyzed [2+ 2] cycloadditions between an alkene and an alkyne

[Jordan, Robert W.; Villeneuve, Karine; Tam, William Journal of Organic Chemistry, 2006 , vol. 71, # 15 p. 5830 - 5833]

More Articles...