FUSED LACTONES AS A ROUTE TO FUNCTIONALIZED 1-SUBSTITUTED INDOLES

Authors
SCHUSTER HF COPPOLA GM
Citation
Hf. Schuster et Gm. Coppola, FUSED LACTONES AS A ROUTE TO FUNCTIONALIZED 1-SUBSTITUTED INDOLES, Journal of heterocyclic chemistry, 31(6), 1994, pp. 1381-1384
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
31
Issue
6
Year of publication
1994
Pages
1381 - 1384
Database
ISI
SICI code
0022-152X(1994)31:6<1381:FLAART>2.0.ZU;2-F
Abstract
Indole lactones 8 and 14 were synthesized as a means of functionalizin g the 1-isopropyl substituent of the indole nucleus. Lactone 8, upon r eduction with diisobutylaluminum hydride, produces lactol 9 which beha ves like a masked hydroxy aldehyde and undergoes a Horner-Emmons react ion with triethyl phosphonoaceate to give alpha,beta-unsaturated ester 3 which possesses a hydroxyl group on the 1-isopropyl moiety.