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Titolo:
IMDAF CYCLOADDITION AS A METHOD FOR THE PREPARATION OF PYRROLOPHENANTHRIDINE ALKALOIDS
Autore:
PADWA A; DIMITROFF M; WATERSON AG; WU TH;
Indirizzi:
EMORY UNIV,DEPT CHEM ATLANTA GA 30322
Titolo Testata:
Journal of organic chemistry
fascicolo: 12, volume: 63, anno: 1998,
pagine: 3986 - 3997
SICI:
0022-3263(1998)63:12<3986:ICAAMF>2.0.ZU;2-L
Fonte:
ISI
Lingua:
ENG
Soggetto:
DIELS-ALDER REACTION; MEISENHEIMER-TYPE ADDUCTS; POLAR TRANSITION-STATE; FURAN-DIENE; HIGH-PRESSURE; RADICAL CYCLIZATION; STEREOCONTROLLED SYNTHESIS; ACID-DERIVATIVES; SOLVENT; RING;
Tipo documento:
Review
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
131
Recensione:
Indirizzi per estratti:
Citazione:
A. Padwa et al., "IMDAF CYCLOADDITION AS A METHOD FOR THE PREPARATION OF PYRROLOPHENANTHRIDINE ALKALOIDS", Journal of organic chemistry, 63(12), 1998, pp. 3986-3997

Abstract

Acylation of 5-amino-2-furancarboxylic acid methyl ester with alkenoyl acid chlorides gives 2-amidofurans that undergo intramolecular Diels-Alder cycloadditions. The reactions occur at 165 degrees C in tolueneor at 100 degrees C when 4 M ethereal LiClO4 was used as the solvent. The resultant dihydroindoles are formed by the nitrogen lone pair assisted ring opening of the initial era-bridged cycloadducts, followed by loss of water. Under certain conditions, alternative cationic cyclization routes become important pathways. Several members of the pyrrolophenanthridine class of alkaloids were obtained by a short, efficient method based on the intramolecular Diels-Alder furan cycloaddition of 2-amidofurans containing a tethered alkenyl group. The resulting dihydroindoles were elaborated in one step to the 1H-pyrrolo[3,2,1-de]phenanthridine ring system by a free radical induced cyclization using bis(tributyltin).

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/04/20 alle ore 19:08:01