Catalogo Articoli (Spogli Riviste)

OPAC HELP

Titolo:
STEREOSELECTIVE SYNTHESIS OF POLYSUBSTITUTED TETRAHYDROFURANS BY RADICAL CYCLIZATION OF EPOXIDES USING A TRANSITION-METAL RADICAL SOURCE - APPLICATION TO THE TOTAL SYNTHESIS OF (+ -)-METHYLENOLACTOCIN AND (+/-)-PROTOLICHESTERINIC ACID/
Autore:
MANDAL PK; MAITI G; ROY SC;
Indirizzi:
INDIAN ASSOC CULTIVAT SCI,DEPT ORGAN CHEM CALCUTTA 700032 W BENGAL INDIA INDIAN ASSOC CULTIVAT SCI,DEPT ORGAN CHEM CALCUTTA 700032 W BENGAL INDIA
Titolo Testata:
Journal of organic chemistry
fascicolo: 9, volume: 63, anno: 1998,
pagine: 2829 - 2834
SICI:
0022-3263(1998)63:9<2829:SSOPTB>2.0.ZU;2-A
Fonte:
ISI
Lingua:
ENG
Soggetto:
GAMMA-BUTYROLACTONES; ORGANIC-SYNTHESIS; BICYCLIC ACETALS; PENICILLIUM SP; ROUTE; DERIVATIVES; (-)-METHYLENOLACTOCIN; METHYLENOLACTOCIN; STEREOCHEMISTRY; FRAGMENTATION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
57
Recensione:
Indirizzi per estratti:
Citazione:
P.K. Mandal et al., "STEREOSELECTIVE SYNTHESIS OF POLYSUBSTITUTED TETRAHYDROFURANS BY RADICAL CYCLIZATION OF EPOXIDES USING A TRANSITION-METAL RADICAL SOURCE - APPLICATION TO THE TOTAL SYNTHESIS OF (+ -)-METHYLENOLACTOCIN AND (+/-)-PROTOLICHESTERINIC ACID/", Journal of organic chemistry, 63(9), 1998, pp. 2829-2834

Abstract

Radical cyclization reactions of substituted alpha-(prop-2-ynyloxy) epoxides using bis(cyclopentadienyl)-titanium(III) chloride as the radical source resulted in polysubstituted tetrahydrofurans. Titanium(III)species were prepared in situ from commercially available titanocene dichloride and zinc dust in tetrahydrofuran, Upon radical cyclization,2-aryl epoxides 3a-e afforded only trans products 4a-e whereas the 2-alkyl epoxides 3f-h formed a mixture of isomeric products 4f-h in a ratio of 5:1. Some of the aryl tetrahydrofuran derivatives have already been used for the synthesis of bioactive furofuran lignans. entyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4f) and decyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4g) have been transformed to two antitumor antibiotics (+/-)-methylenolactocin (1f) and (+/-)-protolichesterinic acid (1g), respectively, in good overall yield.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 28/11/20 alle ore 15:16:23