Total synthesis and stereochemistry of alternaric acid

H Tabuchi, T Hamamoto, S Miki, T Tejima…

Index: Tabuchi; Hamamoto; Miki; Tejima; Ichihara Journal of Organic Chemistry, 1994 , vol. 59, # 17 p. 4749 - 4759

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Citation Number: 45

Abstract

Determination of the stereochemistry and the total synthesis of alternaric acid 1 has been achieved. The stereostructure of 1 has been elucidated by stereoselective synthesis of four diastereoisomers of the C (9)-C (14) fragment 6, which had been obtained as a degradation product during structural studies. Key reactions of the total synthesis of 1 include the Julia olefination of tertiary aldehyde 6 and phenylsulfone 7 and novel one-pot construction of 3- ...