Straightforward synthesis of sphinganines via a serine-derived Weinreb amide

被引：52

作者：

So, RC ^{[1
]}

Ndonye, R ^{[1
]}

Izmirian, DP ^{[1
]}

Richardson, SK ^{[1
]}

Guerrera, RL ^{[1
]}

Howell, AR ^{[1
]}

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 09期

关键词：

D O I：

10.1021/jo030355b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sphinganines can be synthesized in just three steps from easily prepared serine-derived Weinreb amide 4. Pre-deprotonation of the acidic (N-H and O-H) protons of 4 allows for its efficient conversion to amino ketones 5. Such ketones can be selectively reduced to either erythro- or threo-sphinganines. Partially protected sphinganines 11 are also readily accessible in five steps from 4. Thus, Weinreb amide 4 represents one of the most versatile templates described to date for sphinganine synthesis.

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页码：3233 / 3235

页数：3

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