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 ...
