The enynol 2 was transformed into D ‐ erythro ‐sphingosine 11 (7 steps, 46%) and into ceramide 1 (8 steps, 41% overall yield). The key steps were the mono‐epoxidation of the enynol 5 (Ti( t ‐BuO) 4 , (−)‐ D ‐diethyl tartrate, t ‐BuOOH) to 6 (86%, ≥ 98% ee), the regioselective intramolecular opening of the oxirane 6 via the benzylurethane 7 , and the reductive tranformation of the acetylene 9 into the oxazolidinone 10 (Li, EtNH 2 , 88%).
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Julina et al. (1986) studied this question.
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