Total synthesis of A-315675: A potent inhibitor of influenza neuraminidase

被引：74

作者：

Hanessian, S ^{[1
]}

Bayrakdarian, M ^{[1
]}

Luo, XH ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 17期

关键词：

D O I：

10.1021/ja0126226

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise, stereocontrolled, and practical synthesis of a neuraminidase inhibitor consisting of a highly functionalized D-proline scaffold is described. Key features involve a stereocontrolled addition of a propiolate ester to a chiral nonracemic nitrone derived originally from D-serine and the manipulation of acyclic and cyclic motifs en route to the target in 12.8% overall yield over 22 steps, Several crystalline intermediates were suitable for single-crystal X-ray analysis.

引用

页码：4716 / 4721

页数：6

共 115 条

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