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Titolo:
One-step oxidative dimerization of genuine, unprotected naphthylisoquinolines alkaloids to give michellamines and other bioactive quateraryls
Autore:
Bringmann, G; Saeb, W; Mies, J; Messer, K; Wohlfarth, M; Brun, R;
Indirizzi:
Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany Univ Wurzburg Wurzburg Germany D-97074 n Chem, D-97074 Wurzburg, Germany Schweizer Tropeninst, CH-4002 Basel, Switzerland Schweizer Tropeninst Basel Switzerland CH-4002 H-4002 Basel, Switzerland
Titolo Testata:
SYNTHESIS-STUTTGART
fascicolo: 13, , anno: 2000,
pagine: 1843 - 1847
SICI:
0039-7881(200011):13<1843:OODOGU>2.0.ZU;2-K
Fonte:
ISI
Lingua:
ENG
Soggetto:
ACETOGENIC ISOQUINOLINE ALKALOIDS; CONVERGENT TOTAL SYNTHESIS; ANTI-HIV MICHELLAMINES; KORUPENSAMINES-A-D; ANCISTROCLADUS-KORUPENSIS; BIOLOGICAL-ACTIVITY; DIONCOPHYLLINE-B; ANALOGS; ELLAGITANNIN; DIMER;
Keywords:
lead tetraacetate; phenyliodine(III) bis(trifluoroacetate); michellamines; jozimine D; naphthylisoquinoline alkaloids; oxidative phenolic coupling; biaryls;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
44
Recensione:
Indirizzi per estratti:
Indirizzo: Bringmann, G Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany Univ Wurzburg Wurzburg Germany D-97074 74 Wurzburg, Germany
Citazione:
G. Bringmann et al., "One-step oxidative dimerization of genuine, unprotected naphthylisoquinolines alkaloids to give michellamines and other bioactive quateraryls", SYNTHESIS-S, (13), 2000, pp. 1843-1847

Abstract

The first one-step oxidative dimerization of monomeric naphthylisoquinoline alkaloids, using lead tetraacetate or phenyliodine(III) bis(trifluoroacetate) is described, thus avoiding previous 5- or 3-step reaction sequences involving protection, reduction, and deprotection reactions. The method is exemplified for the first nonenzymic direct preparation of michellamines A (la) and C (Ib) from korupensamines A (3a) and B (3b), respectively, and forthe synthesis of the new quateraryl jozimine D (2), the unnatural dimer ofnatural dioncophylline B (5).

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 26/01/21 alle ore 04:26:47