Synthesis and structure of preorganized, C3-symmetric trilactam scaffolds with convergently oriented (S)-acetylthiomethyl appendages

被引：18

作者：

Campbell, JE ^{[1
]}

Englund, EE ^{[1
]}

Burke, SD ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 13期

关键词：

D O I：

10.1021/ol0261480

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient modular synthesis of conformationally preorganized, C-3-symmetric trilactams is reported. The allyl acetate cyclization substrate was synthesized in five steps from Gamer's L-serine-derived aldehyde. After chiral ligand-mediated palladium cyclization, the resulting vinyl hydropyran was transformed into the orthogonally protected amino acids for iterative coupling. The final macrolactamization was accomplished using EDCI/HOBt or HATU/HOAt under high dilution conditions.

引用

页码：2273 / 2275

页数：3

共 13 条

[11] Rhodium-catalyzed cyclohydrocarbonylation: Application to the synthesis of (+)-prosopinine and (-)-deoxoprosophylline [J].