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Titolo:
A practical total synthesis of plaunotol via highly Z-selective Wittig olefination of alpha-acetal ketones
Autore:
Tago, K; Arai, M; 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 THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 13, , anno: 2000,
pagine: 2073 - 2078
SICI:
1470-4358(2000):13<2073:APTSOP>2.0.ZU;2-#
Fonte:
ISI
Lingua:
ENG
Soggetto:
STEREOSELECTIVE SYNTHESIS; HELICOBACTER-PYLORI; CAMPYLOBACTER-PYLORIDIS; GASTRITIS; ALCOHOLS; DISEASE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
28
Recensione:
Indirizzi per estratti:
Indirizzo: Kogen, H 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 , Japan
Citazione:
K. Tago et al., "A practical total synthesis of plaunotol via highly Z-selective Wittig olefination of alpha-acetal ketones", J CHEM S P1, (13), 2000, pp. 2073-2078

Abstract

Plaunotol (1), a known antiulcer drug, is the most important component of the Thai folk medicinal plant, Plau-noi, which has remarkable antipeptic ulcer activity. Recently, it was found that plaunotol (1) has antibacterial activity against Helicobacter pylori, a causative agent in gastric ulcers and gastric adenocarcinoma, for example. In our investigation of the practical synthesis of 1, we have developed an efficient method for stereoselectivesynthesis of trisubstituted olefins via a Z-selective Wittig reaction. Theolefination of readily available aliphatic alpha-acetal ketones with triphenylphosphonium salts in the presence of a potassium base and 18-crown-6 ether proceeded with excellent Z-selectivity. The Z-selective olefination provides a useful method for the construction of a range of trisubstituted olefin moieties; the practical and stereoselective total synthesis of plaunotol (1) was achieved via this Wittig reaction.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 01/12/20 alle ore 00:48:47