Divergent total synthesis of d-ribo-phytosphingosine and l-ribo-phytosphingosine from d-ribose

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• 作者：Jong Soo Chun ; Seung Min Hong ; Tae Hong Jeon ; Sook Jin Park ; Han Pyo Son ; Jun Min Jung ; Young Jae Choi ; In Su Kim ; Young Hoon Jung ; ^{yhjung@skku.edu}
• 关键词：Phytosphingosine ; Amination ; Chlorosulfonyl isocyanate ; Wittig reaction ; Metathesis reaction
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：29 December 2016
• 年：2016
• 卷：72
• 期：52
• 页码：8550-8556
• 全文大小：512 K
• 卷排序：72

文摘

Divergent total synthesis of d-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.