Novel chiral building blocks derived from baker's yeast reduction products: Synthesis and odour of mono- and bicyclic macrolides

Authors
Bollbuck, B Tochtermann, W
Citation
B. Bollbuck et W. Tochtermann, Novel chiral building blocks derived from baker's yeast reduction products: Synthesis and odour of mono- and bicyclic macrolides, TETRAHEDRON, 55(23), 1999, pp. 7191-7208
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
23
Year of publication
1999
Pages
7191 - 7208
Database
ISI
SICI code
0040-4020(19990604)55:23<7191:NCBBDF>2.0.ZU;2-1
Abstract
A number of bicyclic macrolides with two stereogenic centres formally deriv ed from omega-cycloalkyl fatty acids were synthesised by ring enlargement o f cycloalkanones with novel chiral building blocks, easily available from y east reduction products of beta-keto esters. A comparison with structurally related monocyclic macrolides revealed surprising effects of structural va riations on the olfactory properties. (C) 1999 Elsevier Science Ltd. All ri ghts reserved.