Amberlyst-15-catalyzed intramolecular S(N)2 ' oxaspirocyclization of secondary allylic alcohols. Application to the total synthesis of spirocyclic ethers theaspirane and theaspirone

Authors
Young, JJ Jung, LJ Cheng, KM
Citation
Jj. Young et al., Amberlyst-15-catalyzed intramolecular S(N)2 ' oxaspirocyclization of secondary allylic alcohols. Application to the total synthesis of spirocyclic ethers theaspirane and theaspirone, TETRAHEDR L, 41(18), 2000, pp. 3415-3418
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
18
Year of publication
2000
Pages
3415 - 3418
Database
ISI
SICI code
0040-4039(20000429)41:18<3415:AIS'OO>2.0.ZU;2-Z
Abstract
A variety of substituted 1-oxaspiro[4.4]non-6-ene, 1-oxaspiro[4.5]dec-6-ene , 6-oxaspiro[4.5]dec-l-ene and 1-oxaspiro[5.5]undec-7-ene systems have been prepared by utilizing Amberlyst-15-catalyzed intramolecular S(N)2' oxaspir ocyclizations of secondary allylic alcohols under mild reaction conditions in quantitative yields. This oxaspirocyclization was applied to the total s ynthesis of theaspirane and theaspirone from beta-ionone in five steps. (C) 2000 Elsevier Science Ltd. All rights reserved.