A SHORT SYNTHESIS OF THE UNUSUAL AMINO-ACID OF CYCLOSPORINE (4R)-4-[(E)-2-BUTENYL]-4,N-DIMETHYL-L-THREONINE (MEBMT)

Authors
SAVIGNAC M DURAND JO GENET JP
Citation
M. Savignac et al., A SHORT SYNTHESIS OF THE UNUSUAL AMINO-ACID OF CYCLOSPORINE (4R)-4-[(E)-2-BUTENYL]-4,N-DIMETHYL-L-THREONINE (MEBMT), Tetrahedron : asymmetry, 5(4), 1994, pp. 717-722
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
4
Year of publication
1994
Pages
717 - 722
Database
ISI
SICI code
0957-4166(1994)5:4<717:ASSOTU>2.0.ZU;2-U
Abstract
MeBmt 1 was prepared in four steps from the optically pure (2Z, 4R) 4- methyloct-6-yn-2-en-1-ol 8, Z allylic alcohol containing an alkynyl gr oup at the gamma position. The two stereogenic centers C-2 and C-3 in the product were controlled using Sharpless' epoxidation and subsequen t ring opening at C-2 of the epoxy acid 10 with methylamine.