A highly diastereoselective approach to conformationally constrained serine analogues:: Synthesis of an α-amino-β-hydroxycyclohexenecarboxylic acid and derivatives

被引：19

作者：

Clerici, F ^{[1
]}

Gelmi, ML ^{[1
]}

Gambini, A ^{[1
]}

机构：

[1] Univ Milan, Fac Farm, Ist Chim Organ, I-20133 Milan, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 16期

关键词：

D O I：

10.1021/jo9821877

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereospecific synthesis of alpha-amino-beta-hydroxycyclohexenecarboxylic acid (7) was found starting from 4-chloromethylene-5(4H)-oxazolone (1) which reacted with 2,3-dimethylbutadiene in the presence of EtAlCl2. The Diels-Alder reaction gave two diastereoisomeric cycloadducts 2 and 3, depending on the configuration of the starting dienophile 1. Compounds 2a and 3 were transformed into the ester 4 and the oxazoline 6, respectively, by reaction with MeOH and p-TSA. The reaction of 2a and 3 with dimethylamine in ethanol solution gave the corresponding amides 8 and 9, respectively, which were transformed into the bicyclic oxazoline 10 on reaction with Na2CO3 in acetonitrile. On acidic hydrolysis both oxazolines 6 and 10 were transformed into alpha-amino-beta-hydroxycyclohexenecarboxylic acid (7) that includes the serine skeleton.

引用

页码：5764 / 5767

页数：4

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