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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
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- 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