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