Moenomycin analogues with modified lipid side chains from indium-mediated Barbier-type reactions

Authors
Vogel, S Stembera, K Hennig, L Findeisen, M Giesa, S Welzel, P Lampilas, M
Citation
S. Vogel et al., Moenomycin analogues with modified lipid side chains from indium-mediated Barbier-type reactions, TETRAHEDRON, 57(19), 2001, pp. 4139-4146
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
19
Year of publication
2001
Pages
4139 - 4146
Database
ISI
SICI code
0040-4020(20010507)57:19<4139:MAWMLS>2.0.ZU;2-Y
Abstract
From moenomycin A both the chromophore part and the Lipid side chain were d egraded by ozonolysis to give an analogue with a glycolaldehyde unit in 2-p osition of the glyceric acid moiety. The aldehyde was converted to a number of homoallylic alcohols by indium-mediated Barbier-type reactions with all ylic and benzylic halides. With exception of the phytyl bromide-derived rea ction product all compounds were antibiotically inactive. (C) 2001 Elsevier Science Ltd. All rights reserved.