New synthetic methodology for ring expansion of n-sized conjugated cycloalkenones into homoallylic n+3 lactones: three-step synthesis of fragrant phoracantholide

Authors
Posner, GH Wang, Q Halford, BA Elias, JS Maxwell, JP
Citation
Gh. Posner et al., New synthetic methodology for ring expansion of n-sized conjugated cycloalkenones into homoallylic n+3 lactones: three-step synthesis of fragrant phoracantholide, TETRAHEDR L, 41(49), 2000, pp. 9655-9659
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
49
Year of publication
2000
Pages
9655 - 9659
Database
ISI
SICI code
0040-4039(200012)41:49<9655:NSMFRE>2.0.ZU;2-D
Abstract
Under the influence of Lewis acidic boron trifluoride-diethyl etherate, epo xides are activated sufficiently to undergo rapid nucleophilic opening by k etone enolate ions at -78 degreesC, forming useful gamma -lactols. Applicat ion of this protocol to n+3 ring expansion features one-flask, multicompone nt, sequential reactions. (C) 2000 Elsevier Science Ltd. All rights reserve d.