Anionic [4+2]cycloaddition - Retro [4+2]cycloaddition strategy in the synthesis of psoralen and its isoster

Authors
Bandyopadhyay, M Datta, K Mal, D
Citation
M. Bandyopadhyay et al., Anionic [4+2]cycloaddition - Retro [4+2]cycloaddition strategy in the synthesis of psoralen and its isoster, J INDIAN CH, 76(11-12), 1999, pp. 551-556
Citations number
12
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
551 - 556
Database
ISI
SICI code
0019-4522(199911/12)76:11-12<551:A[-R[S>2.0.ZU;2-#
Abstract
Furan-1,4-dipolar agents 7 and 16e, prepared in few steps from commercially available furoates, have been annulated with bicyclopentadienone 2 to prov ide pentacyclic frameworks 8 and 17 respectively. Subsequent transformation s of 8 and 17 through retro-Diels-Alder reaction and indenol-indanone rearr angement have furnished psoralen precursors 14 and 19. Similarly, oxaindace none 23 has been prepared in good yield from 21.