An efficient high-yield synthesis of D-ribo-phytosphingosine.
[Structure: see text] [4R-[4alpha(S),5alpha]]-2,2-Dimethyl-4-(2-oxo-5-vinyl[1,3]dioxolan-4-yl)oxazolidine-3-carboxylic acid tert-butyl ester 5a, obtained in excellent yield and diastereoselectivity by the alpha-hydroxyallylation of the Garner aldehyde (4), is exploited in a novel high-yield synthesis of D-ribo-phytosphingosine (8), using microwave-enhanced cross metathesis as the key step in the chain elongation.
Lombardo
Marco
M
Dipartimento di Chimica G. Ciamician, Università di Bologna, via Selmi 2, 40126, Bologna, Italy. marco.lombardo@unibo.it
Capdevila
Montse Guiteras
MG
Pasi
Filippo
F
Trombini
Claudio
C
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; C012491:phytosphingosine; D013110:Sphingosine