Spiroannulation of a cyclopentane ring. Synthesis of spiro[4.n](n+5)alk-2-en-1-ones

Authors
Srikrishna, A Kumar, PP
Citation
A. Srikrishna et Pp. Kumar, Spiroannulation of a cyclopentane ring. Synthesis of spiro[4.n](n+5)alk-2-en-1-ones, J INDIAN CH, 76(11-12), 1999, pp. 521-526
Citations number
37
Categorie Soggetti
Chemistry
Journal title
JOURNAL OF THE INDIAN CHEMICAL SOCIETY
ISSN journal
00194522 → ACNP
Volume
76
Issue
11-12
Year of publication
1999
Pages
521 - 526
Database
ISI
SICI code
0019-4522(199911/12)76:11-12<521:SOACRS>2.0.ZU;2-#
Abstract
A methodology based on Claisen rearrangement-Wacker oxidation and intramole cular aldol condensation strategy starting from cyclic ketones leading to s piro[4.n](n+5)alk-2-en-1-ones has been developed. Thus one-pot Claisen rear rangement of the alkyl alcohols 6a-c furnished the aldehydes 8a-c, which on regiospecific oxidation using Wacker conditions generated the keto-aldehyd es 9a-c. Finally, intramolecular aldol condensation transformed the keto-al dehydes 9a-c into spiroannulated products 10a-c.