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Titolo:
Practical and effective total synthesis of plaunotol via novel and stereoselective method for construction of tri-substituted olefins
Autore:
Tago, K; Kogen, H;
Indirizzi:
Sankyo Co Ltd, Exploratory Chem Res Labs, Shinagawa Ku, Tokyo 1408710, Japan Sankyo Co Ltd Tokyo Japan 1408710 bs, Shinagawa Ku, Tokyo 1408710, Japan
Titolo Testata:
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
fascicolo: 10, volume: 59, anno: 2001,
pagine: 971 - 984
SICI:
0037-9980(200110)59:10<971:PAETSO>2.0.ZU;2-6
Fonte:
ISI
Lingua:
JPN
Soggetto:
Z-UNSATURATED ESTERS; SELECTIVE WITTIG OLEFINATION; SQUALENE SYNTHASE INHIBITOR; WADSWORTH-EMMONS REACTION; HELICOBACTER-PYLORI; TRISUBSTITUTED ALKENES; SCHIZOPHYLLUM-COMMUNE; STRUCTURE ELUCIDATION; PHEROMONE SYNTHESIS; GASTRIC-CANCER;
Keywords:
plaunotol; Hericobacter pylori; Horner-Wadsworth-Emmons reaction; (E)-alpha-bromoacrylate; Wittig reaction; alpha-acetalketone;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
67
Recensione:
Indirizzi per estratti:
Indirizzo: Tago, K Sankyo Co Ltd, Exploratory Chem Res Labs, Shinagawa Ku, 2-58 Hiromachi 1 Chome, Tokyo 1408710, Japan Sankyo Co Ltd 2-58 Hiromachi 1 Chome Tokyo Japan 1408710 0, Japan
Citazione:
K. Tago e H. Kogen, "Practical and effective total synthesis of plaunotol via novel and stereoselective method for construction of tri-substituted olefins", J SYN ORG J, 59(10), 2001, pp. 971-984

Abstract

Plaunotol, a known antiulcer drug, has antibacterial activities against Hericobacter pylori. We developed the efficient and practical synthesis of plaunotol and its derivatives. In order to construct C6-C7 tri-substituted allylic alcohol with high stereo selectivity, the Horner-Wadsworth-Emmons reaction with novel reagent and the Wittig reaction with alpha -acetalketones were developed. These methods were found to give a range of tri-substitutedolefin moieties. Using (E)-alpha -bromoacrylate as a key intermediate, which was prepared from novel reagent-methyl bis(2,2, 2-trifluoroethoxy)bromophosphonoacetate, the most effective route of plaunotol synthesis via Suzukicross-coupling was achieved. Moreover the most practical synthesis of plaunotol was achieved via Z-selective Wittig reaction using alpha -acetalketone. In search for high antibacterial activities, we designed plaunotol thiourea derivatives and diol derivatives. These derivatives were synthesized regioselectively using our effective synthetic route to plaunotol. Their antibacterial activities against Hericobactor pylori are described and the C1-phenethylthiourea derivative was the most potent antibacterial agent.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 01/12/20 alle ore 00:36:07