Stereochemical definition and chirospecific synthesis of the peptide deformylase inhibitor Sch 382583

被引：14

作者：

Coats, RA ^{[1
]}

Lee, SL ^{[1
]}

Davis, KA ^{[1
]}

Patel, KM ^{[1
]}

Rhoads, EK ^{[1
]}

Howard, MH ^{[1
]}

机构：

[1] DuPont Crop Protect, Stine Haskell Res Ctr, Newark, DE 19711 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 05期

关键词：

D O I：

10.1021/jo035667t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The recently reported natural product Sch 382583 (1), an inhibitor of peptide deformylase, has been synthesized in 16 steps from commercially available starting materials. The three chiral centers were set by a combination of chiral auxiliary and chiral pool approaches. The succinate 5 and piperazic acid 9 moieties were obtained by Evans oxazolidinone imide enolate alkylation and hydrazination/cyclization, respectively, and the aminohexanone side chain 13 was prepared via Grignard substitution of the Weinreb amide derived from L-valine. Spectroscopic data for the resulting synthetic material, compared with the data reported for the natural product, established that the previously unassigned valine ketone stereocenter (C-4) has the S-configuration.

引用

页码：1734 / 1737

页数：4

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