Enantioselective synthesis of lyxo-(2R,3R,4R)-C-18-phytosphingosine using double stereodifferentiation

Authors
Martin, C Prunck, W Bortolussi, M Bloch, R
Citation
C. Martin et al., Enantioselective synthesis of lyxo-(2R,3R,4R)-C-18-phytosphingosine using double stereodifferentiation, TETRAHEDR-A, 11(7), 2000, pp. 1585-1592
Citations number
47
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
7
Year of publication
2000
Pages
1585 - 1592
Database
ISI
SICI code
0957-4166(20000420)11:7<1585:ESOLUD>2.0.ZU;2-2
Abstract
lyxo-C-18-Phytosphingosine can be synthesized by the cis-dihydroxylation of an (E)-allylic trichloroacetamide obtained by an Overman rearrangement. A double stereodifferentiation using AD-mix-beta and an enantiomerically enri ched (S)-allylic trichloroacetamide allowed the first synthesis of lyxo-(2R ,3R,4R)-C-18-phytosphingosine with high diastereoselectivity (de = 94%) and excellent enantioselectivity (ee = 93%). This sphingosine was fully charac terized by the physical and spectral data of the corresponding tetraacetate . (C) 2000 Elsevier Science Ltd. All rights reserved.