88642-46-0Relevant articles and documents
Synthesis of phalluside-1 and Sch II using 1,2-metallate rearrangements
Black, Fiona J.,Kocienski, Philip J.
supporting information; experimental part, p. 1188 - 1193 (2010/06/15)
(4E,8E,10E)-9-Methyl-4,8,10-sphingatrienine, a core component of marine sphingolipids, was synthesised for the first time using a copper(i)-mediated 1,2-metallate rearrangement of a lithiated glycal as a key step. It was converted to phalluside-1, a cereb
Efficient stereocontrolled synthesis of sphingadienine derivatives
Murakami, Teiichi,Hirono, Reiko,Furusawa, Kiyotaka
, p. 9233 - 9241 (2007/10/03)
Sphinga-4,8-dienines, principal long-chain bases of glycolipids in plants and fungi, were efficiently synthesized from l-serine. Hydrozirconation of pentadec-5-en-1-ynes followed by ZnBr2-catalyzed addition to Garner's aldehyde afforded protected sphinga-4,8-dienines stereoselectively. The (2S,3R,4E,8E)-9-methyl-sphingadienine derivative was then coupled with 2(R)-acetoxypalmitic acid derivative prepared via asymmetric dihydroxylation to give a protected ceramide, which was converted into the corresponding glucocerebroside in two steps.
SYNTHESIS OF (4E,8E,2S,3R,2'R)-N-2'-HYDROXYHEXADECANOYL-1-O-β-D-GLUCOPYRANOSYL-9-METHYL-4,8-SPHINGADIENINE, THE FRUITING-INDUCING CEREBROSIDE IN A BASIDIOMYCETE SCHIZOPHYLLUM COMMUNE
Mori, Kenji,Funaki, Yuji
, p. 2379 - 2386 (2007/10/02)
The title compound was synthesized by employing (R)-2-aminohexadecanoic acid, D-glucose and (S)-serine as the chiral sources, and the synthetic sample was found to be chemically and biologically identical with the fruiting-inducing cerebroside isolated fr