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Titolo:
Application of furanyl carbamate cycloadditions toward the synthesis of hexahydroindolinone alkaloids
Autore:
Padwa, A; Brodney, MA; Dimitroff, M; Liu, B; Wu, TH;
Indirizzi:
Emory Univ, Dept Chem, Atlanta, GA 30322 USA Emory Univ Atlanta GA USA 30322 ry Univ, Dept Chem, Atlanta, GA 30322 USA
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 9, volume: 66, anno: 2001,
pagine: 3119 - 3128
SICI:
0022-3263(20010504)66:9<3119:AOFCCT>2.0.ZU;2-6
Fonte:
ISI
Lingua:
ENG
Soggetto:
DIELS-ALDER REACTION; FORMAL TOTAL SYNTHESIS; OLEFIN METATHESIS; ORGANIC-SYNTHESIS; N-ALLYLTRICHLOROACETAMIDES; DENDROBINE SKELETON; LEWIS-ACIDS; (+/-)-DENDROBINE; CYCLIZATION; DIENE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
90
Recensione:
Indirizzi per estratti:
Indirizzo: Padwa, A Emory Univ, Dept Chem, 1515 Pierce Dr, Atlanta, GA 30322 USA Emory Univ 1515 Pierce Dr Atlanta GA USA 30322 anta, GA 30322 USA
Citazione:
A. Padwa et al., "Application of furanyl carbamate cycloadditions toward the synthesis of hexahydroindolinone alkaloids", J ORG CHEM, 66(9), 2001, pp. 3119-3128

Abstract

A convenient. synthesis of various substituted hexahydroindolinones has been achieved by an intramolecular Diels-Alder cycloaddition reaction (IMDAF)of furanyl carbamates bearing tethered alkenyl,groups. The initially formed [4 + 2]-cycloadduct undergoes nitrogen-assisted ring opening followed by deprotonation of the resulting zwitterion to give the rearranged ketone. The stereochemical outcome of the IMDAF cycloaddition has the sidearm of the tethered alkenyl group oriented syn with respect to the oxygen bridge. A synthetic route to (+/-)-mesembrane and (+/-)-crinane was accomplished using this methodology. It was possible to carry out a stereoselective reduction of the initially formed hexahydroindolinone ring to produce the cis-3a-aryl-hydroindole skeleton. A related [4 + 2] -cycloaddition/rearrangement sequence was also used for a formal synthesis of the Chinese ornamental orchid (/-)-dendrobine. The tricylic alkaloid core was formed stereoselectivity from the thermolysis of N-[(2-methyl-2-cyclopentenyl)methyl]-N-(4-isopropyl-furan-2-yl)carbamic acid tert-butyl ester. Kende's advanced intermediate 33was prepared in seven additional steps by standard transformations, thereby completing a formal synthesis of (+/-)-dendrobine.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 28/03/20 alle ore 23:13:08