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Enantioselective Synthesis of D ‐ erythro ‐Sphingosine and of Ceramide
Author(s) -
Julina Radomir,
Herzig Thomas,
Bernet Bruno,
Vasella Andrea
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690216
Subject(s) - chemistry , sphingosine , ceramide , enantioselective synthesis , regioselectivity , diastereomer , stereochemistry , yield (engineering) , intramolecular force , organic chemistry , biochemistry , catalysis , receptor , apoptosis , materials science , metallurgy
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%).