AN EFFICIENT BIOMIMETIC SYNTHESIS OF SOME MARINE SPONGE TYROSINE METABOLITES

被引：13

作者：

BOEHLOW, TR ^{[1
]}

SPILLING, CD ^{[1
]}

机构：

[1] UNIV MISSOURI,DEPT CHEM,ST LOUIS,MO 63121

来源：

NATURAL PRODUCT LETTERS | 1995年 / 7卷 / 01期

基金：

美国国家科学基金会;

关键词：

SPONGE METABOLITES; TYROSINE; OXIMES; OXIDATION; BROMINATION;

D O I：

10.1080/10575639508043179

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The oxidation of tyrosine ethyl ester and O-benzyl protected O-tyrosine methyl ester with either sodium tungstate/hydrogen peroxide or DMD gave the corresponding tyrosine oximes in high yields. Controlled bromination of the aromatic ring gave either the monobromo oxime, the dibromo oxime, or the spiroisoxazoline depending upon reaction conditions. The bromo tyrosine oximes were further transformed into the naturally occurring nitriles by base hydrolysis of the oximino esters and decarboxylation of the resulting oximino acids with trifluoroacetic acid in CH2Cl2.

引用

页码：1 / 6

页数：6

共 36 条

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