Asymmetric oxidative cyclization of o-phenolic oxime-esters: First synthesis of enantiomerically enriched spiroisoxazoline methyl esters

被引：40

作者：

Murakata, M ^{[1
]}

Tamura, M ^{[1
]}

Hoshino, O ^{[1
]}

机构：

[1] SCI UNIV TOKYO,FAC PHARMACEUT SCI,SHINJUKU KU,TOKYO 162,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 13期

关键词：

D O I：

10.1021/jo970082i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the synthesis of enantiomerically enriched cyclohexadienone spiroisoxazoline (-)-2a has been described. Asymmetric intramolecular oxidative cyclization of the o-phenolic oxime-ester Ic using a novel optically active tertiary alcohol (-)-3 as a chiral auxiliary proceeded smoothly to afford cyclohexadienone spiroisoxazoline 2c in 83% yield. Opitcally active tertiary alcohol (-)-3 was synthesizied, from racemic (1S*, 8R*, 9R*, 10R*)-8-phenyl-1-decalol (4) by optical resolution. Removal of the chiral auxiliary in 2c with CF3COOH followed by methylation gave methyl ester (-)-2a in 74% ee (71% chemical yield) having S-configuration. The absolute configuration of 2a was determined by the synthesis of the marine natural product (+)-aerothionin.

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页码：4428 / 4433

页数：6

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