The Journal of organic chemistry

Asymmetric synthesis of d-ribo-phytosphingosine from 1-tetradecyne and (4-methoxyphenoxy) acetaldehyde

Z Liu, HS Byun, R Bittman

文献索引：Liu, Zheng; Byun, Hoe-Sup; Bittman, Robert Journal of Organic Chemistry, 2010 , vol. 75, # 13 p. 4356 - 4364

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被引用次数: 21

摘要

An asymmetric synthesis of d-ribo-phytosphingosine (1) was achieved by utilizing the ProPhenol (12)-catalyzed alkynylation of unsaturated aldehyde 8 to afford allylic propargylic alcohol (S)-6 followed by asymmetric epoxidation and opening of propargylic epoxy alcohol anti-5 with NaN3/NH4Cl. Deprotection and reduction of the resulting acyclic azide 3 then gave 1. Alkyne− azide 3 was subjected to an intramolecular click reaction, generating a ...