Divergent total synthesis of D-ribo-phytosphingosine and L-ribo-phytosphingosine from D-ribose

被引：9

作者：

Chun, Jong Soo ^{[1
]}

Hong, Seung Min ^{[1
]}

Jeon, Tae Hong ^{[1
]}

Park, Sook Jin ^{[1
]}

Son, Han Pyo ^{[1
]}

Jung, Jun Min ^{[1
]}

Choi, Young Jae ^{[1
]}

Kim, In Su ^{[1
]}

Jung, Young Hoon ^{[1
]}

机构：

[1] Sungkyunkwan Univ, Sch Pharm, Suwon 440746, South Korea

来源：

TETRAHEDRON | 2016年 / 72卷 / 52期

基金：

新加坡国家研究基金会;

关键词：

Phytosphingosine; Amination; Chlorosulfonyl isocyanate; Wittig reaction; Metathesis reaction; CHLOROSULFONYL ISOCYANATE; DIASTEREOSELECTIVE AMINATION; STEREOSELECTIVE AMINATION; ASYMMETRIC-SYNTHESIS; EFFICIENT; ETHERS; SPHINGANINE; CERAMIDE; ROUTE;

D O I：

10.1016/j.tet.2016.11.018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Divergent total synthesis of o-ribo-phytosphingosine (1) and L-ribo-phytosphingosine (2) was achieved from readily available D-ribose via cross-metathesis reaction, Wittig reaction, and diastereoselective amination reaction of allylic ethers using chlorosulfonyl isocyanate (CSI) as the key steps. As results, reactions of anti-1,2-dibenzyl ethers 11 and 16 with chlorosulfonyl isocyanate afforded exclusively anti 1,2 -amino alcohols 12 and 17 with diastereoselectivity of 32:1 and 31:1 in 75% and 76% yields, respectively. These results could be explained by the neighboring group effect, leading to retention of stereochemistry. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：8550 / 8556

页数：7

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