Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-N-Hexanoyldihydrosphingosine

被引：17

作者：

Nagamalla, Someshwar ^{[1
]}

Paul, Debobrata ^{[1
]}

Mague, Joel T. ^{[2
]}

Sathyamoorthi, Shyam ^{[1
]}

机构：

[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA

[2] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 33期

基金：

美国国家卫生研究院;

关键词：

STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; 2,3-EPOXY ALCOHOLS; EFFICIENT; SPHINGANINE; CLAVAMINOL; EPOXIDES; ALKENES; OLEFINS;

D O I：

10.1021/acs.orglett.2c02496

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present a unique strategy for the synthesis of vicinal amino alcohols. Ring opening of aziridines with pendant silanols is compatible with a range of substrates. To engage productively in ring opening, the aziridine must be at least mildly activated, and a variety of such N-substituents are tolerated. The utility of this methodology is highlighted in facile preparations of the natural products (+/-)-Clavaminol H, (+/-)-dihydrosphingosine, and (+/-)-N-hexanoyldihydrosphingosine as well as a natural product analogue (+/-)-des-acetyl-Clavaminol H.

引用

页码：6202 / 6207

页数：6

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