Chemoenzymatic synthesis and synthetic application of enantiopure aminocyclopentenols:: Total synthesis of carbocyclic (+)-uracil polyoxin C and its α-epimer

被引：66

作者：

Li, FZ ^{[1
]}

Brogan, JB ^{[1
]}

Gage, JL ^{[1
]}

Zhang, DY ^{[1
]}

Miller, MJ ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 13期

关键词：

D O I：

10.1021/jo0496796

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbocyclic uracil polyoxin C (+)-2 and its alpha-epimer (-)-3 were synthesized in an efficient fashion from cis-4-(N-tert-butylcarbamoyl)cyclopent-2-en-1-ol (+/-)-7. The synthesis incorporates a concise, inexpensive chemoenzymatic synthesis of enantiopure aminocyclopentenols, a Pd(O)-catalyzed substitution reaction, and a mild reduction of an alpha-nitro ester by TiCl3/sodium borohydride. Significantly, this process demonstrates the synthetic utility of the versatile enantiopure aminocyclopentenol building block 4.

引用

页码：4538 / 4540

页数：3