A SHORT ASYMMETRIC-SYNTHESIS OF N-ALPHA-FMOC-N-DELTA-BOC-ALPHA-METBYL-D-ORNITHINE

被引：14

作者：

SHRADER, WD

MARLOWE, CK

机构：

[1] UNIV CALIF BERKELEY, DEPT CHEM, BERKELEY, CA 94720 USA

[2] CHIRON CORP, EMERYVILLE, CA 94608 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1995年 / 5卷 / 19期

关键词：

D O I：

10.1016/0960-894X(95)00383-5

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The title compound was synthesized in six steps from N-Cbz-L-alanine through asymmetric alkylation of a cis-2-phenyl-4-methyl-5-oxazolidinone with tert-butyl 4-iodobutyrate. The cis-2-phenyl-4-methyl-5-oxazolidinone was obtained via a new BF3 . Et(2)O mediated condensation with benzaldehyde dimethyl acetal and N-Cbz-L-alanine. The delta-carboxylate was converted to the delta-N-Boc derivative 5 through a Curtius rearrangement. Hydrogenation yielded N-delta-Boc-alpha-methyl-D-ornithine 6, which was protected as the alpha-N-Fmoc derivative for incorporation into solid phase peptide synthesis.

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页码：2207 / 2210

页数：4

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