Conformationally constrained serine analogues: Synthesis of new 2-amino-3-hydroxynorbornanecarboxylic acid 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, Ctr Interuniv Ric Reaz Pericicl & Sintesi Sistemi, I-20133 Milan, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 19期

关键词：

D O I：

10.1021/jo000595g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of the new oxazolone 2, functionalized with the ethoxycarbonyloxy group on methylenic carbon, is presented, starting from 4-hydroxymethylenoxazolone 1 and ethyl chlorocarbonate. Oxazolone 2 was reacted with cyclopentadiene in the presence of EtAlCl2, giving the two diastereoisomeric cycloadducts exo-3 and endo-3 in a 70:30 ratio. Selective hydrolysis of the lactone ring (THF, HCl) gave the corresponding acids 5 and 6 which were transformed into hydroxyacid derivatives 7 and 8, respectively, operating in an ethanolic solution of Me2NH. The new 3-hydroxy2-aminonorbornane-2-carboxylic acids 11 and 12, in which the serine skeleton is included, were obtained by reduction of acids 5 and 6 to derivatives 9 and 10 and a subsequent hydrolysis with HCl.

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页码：6138 / 6141

页数：4

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