High-Yielding Synthesis of Sphingoid-Type Bases

被引：52

作者：

Seguin, Catherine ^{[1
]}

Ferreira, Franck ^{[1
]}

Botuha, Candice ^{[1
]}

Chemla, Fabrice ^{[1
]}

Perez-Luna, Alejandro ^{[1
]}

机构：

[1] Univ Paris 06, UPMC, CNRS, Inst Parisien Chim Mol FR 2769,UMR 7201, F-75005 Paris, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 18期

关键词：

D-ERYTHRO-SPHINGOSINE; OLEFIN CROSS-METATHESIS; N-TERT-BUTANESULFINYLAZIRIDINES; D-RIBO-PHYTOSPHINGOSINE; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; RACEMIC ALLENYLZINC; COMMON INTERMEDIATE; EFFICIENT SYNTHESIS;

D O I：

10.1021/jo901567q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient methodology for the synthesis of sphingoid-type bases is reported. It involves the stereoselective addition of a racemic 3-alkoxy allenylzinc to enantiopure N-tert-butylsulfinyl imines and a cross-metathesis reaction as the key steps. It has been successfully applied to the syntheses of sphinganine and naturally occurring bioactive related compounds, among which the hydrolysis product of clavaminol H and two spisulosines. All of these compounds have been prepared in six steps from N-tert-butylsulfinyl imines in high overall yields (>56%).

引用

页码：6986 / 6992

页数：7

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