TOTAL SYNTHESIS AND STEREOCHEMISTRY OF ALTERNARIC ACID

被引：51

作者：

TABUCHI, H ^{[1
]}

HAMAMOTO, T ^{[1
]}

MIKI, S ^{[1
]}

TEJIMA, T ^{[1
]}

ICHIHARA, A ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC AGR,DEPT BIOSCI & CHEM,SAPPORO 060,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 17期

关键词：

D O I：

10.1021/jo00096a016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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-acyl-4-hydroxy-5,6-dihydro-2-pyrone via Fries-type rearrangement of the O-enol acyl group of beta-keto-delta-valerolactone toward the a-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1. The modified Fries-type rearrangement method has also been extended to the synthesis of some other compounds containing a tricarbonylmethane structure.

引用

页码：4749 / 4759

页数：11

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