Enantioselective Synthesis of (+)-L-733,060 and (+)-CP-99,994: Application of an Ireland-Claisen Rearrangement/Michael Addition Domino Sequence

被引：38

作者：

Garrido, Narciso M. ^{[1
]}

Garcia, Mercedes ^{[1
]}

Rosa Sanchez, M. ^{[1
]}

Diez, David ^{[1
]}

Urones, Julio G. ^{[1
]}

机构：

[1] Univ Salamanca, Dept Quim Organ, E-37008 Salamanca, Spain

来源：

SYNLETT | 2010年 / 03期

关键词：

domino reactions; chiral piperidines; asymmetric synthesis; chiral auxiliaries; delta-amino acids; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; ACID; ACTIVATION; REDUCTION; L-733,060; OXIDATION; REAGENTS; KETONES;

D O I：

10.1055/s-0029-1219200

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient asymmetric synthesis of (+)-L-733,060, (-)(2S,3R)-1 and (+)-CP-99,994, starting from a Baylis-Hillman adduct, is described. The key steps include a novel domino reaction: stereoselective Ireland-Claisen rearrangement, asymmetric Michael addition, and piperidone ring formation through a one-pot reaction hydrogenolysis/lactamization and a stereoselective inversion of a hydroxy group.

引用

页码：387 / 390

页数：4

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