Highly diastereoselective desymmetrizations of cyclo(Pro,Pro): An enantioselective strategy toward phakellstatin and phakellin

被引：45

作者：

Poullennec, KG ^{[1
]}

Kelly, AT ^{[1
]}

Romo, D ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 16期

关键词：

D O I：

10.1021/ol026140q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Monoenolates of C-2-symmetric, proline-derived piperazine-2,5-diones were generated and trapped with a variety of electrophiles to produce, in a highly diastereoselective fashion, functionalized diketopiperazines (DKPs). These reactions provide the basis for an asymmetric, desymmetrization strategy toward the marine alkaloids phakellstatin and phakellin, The relative stereochemistry of the functionalized DKPs was confirmed by single-crystal X-ray analysis and/or NOE experiments. Bis-functionalization of the DKPs was also found to proceed with high levels of diastereoselectivity.

引用

页码：2645 / 2648

页数：4

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