Helvetica Chimica Acta p. 368 - 373 (1986)
Update date:2022-08-03
Topics:
Julina, Radomir
Herzig, Thomas
Bernet, Bruno
Vasella, Andrea
The enynol 2 was transformed into D-erythro-sphingosine 11 (7 steps, 46 percent) and into ceramide 1 (8 step, 41 percent overall yield).The key steps were the mono-epoxidation of the enynol 5 (Ti(t-BuO)4, (-)-D-diethyl tartrate, t-BuOOH) to 6 (86percent, >/= 98percent ee), the regioselective intramolecular opening of the oxirane 6 via the benzylurethane 7, and the reductive transformation of the acetylene 9 into the oxazolidinone 10 (Li, EtNH2, 88 percent).
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