Stereocontrolled introduction of an amino group at C-6 of D-galactose via (3,3)-sigmatropic rearrangements - novel synthesis of lincosamine and 7-epi-lincosamine precursors

Authors
Gonda, J Zavacka, E Budesinsky, M Cisarova, I Podlaha, J
Citation
J. Gonda et al., Stereocontrolled introduction of an amino group at C-6 of D-galactose via (3,3)-sigmatropic rearrangements - novel synthesis of lincosamine and 7-epi-lincosamine precursors, TETRAHEDR L, 41(4), 2000, pp. 525-529
Citations number
33
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
4
Year of publication
2000
Pages
525 - 529
Database
ISI
SICI code
0040-4039(20000122)41:4<525:SIOAAG>2.0.ZU;2-D
Abstract
A new and stereoselective route to the aminoglycoside components of the ant ibiotics lincomycin and clindamycin is presented, The key step involves dia stereoselective introduction of the amino group at C-6 of D-galactose by (3 ,3)-sigmatropic rearrangements of the corresponding allylic (Z)-trifluoroac etimidate and (Z)- and (E)-allylic thiocyanates. Epoxidation of the resulti ng trifluoroacetamide with m-CPBA led to the epoxide with high threo-select ivity. (C) 2000 Elsevier Science Ltd. All rights reserved.