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Titolo:
Total syntheses of (S)-(-)-zearalenone and lasiodiplodin reveal superior metathesis activity of ruthenium carbene complexes with imidazol-2-ylidene ligands
Autore:
Furstner, A; Thiel, OR; Kindler, N; Bartkowska, B;
Indirizzi:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany Max Planck Inst Kohlenforsch Mulheim Germany D-45470 70 Mulheim, Germany
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 23, volume: 65, anno: 2000,
pagine: 7990 - 7995
SICI:
0022-3263(20001117)65:23<7990:TSO(AL>2.0.ZU;2-U
Fonte:
ISI
Lingua:
ENG
Soggetto:
RING-CLOSING-METATHESIS; LOW-VALENT TITANIUM; ACID TYPE MACROLIDES; OLEFIN METATHESIS; ENANTIOSELECTIVE SYNTHESIS; CARBONYL-COMPOUNDS; COUPLING REACTIONS; ORGANIC-SYNTHESIS; IMIDAZOLIN-2-YLIDENE LIGANDS; INTRAMOLECULAR ALKYLATION;
Tipo documento:
Review
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
109
Recensione:
Indirizzi per estratti:
Indirizzo: Furstner, A Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany Max Planck Inst Kohlenforsch Mulheim Germany D-45470 Germany
Citazione:
A. Furstner et al., "Total syntheses of (S)-(-)-zearalenone and lasiodiplodin reveal superior metathesis activity of ruthenium carbene complexes with imidazol-2-ylidene ligands", J ORG CHEM, 65(23), 2000, pp. 7990-7995

Abstract

Total syntheses of the bioactive orsellinic acid derivatives zearalenone 3and lasiodiplodin 1 are reported based on a ring-closing metathesis (RCM) reaction of styrene precursors as the key steps. These and closely related macrocyclizations are catalyzed with high efficiency by the "second generation" ruthenium carbene catalyst 5 bearing a N-heterocyclic carbene ligand, whereas the standard Grubbs carbene 4 fails to afford any cyclized product. Only the (E)-isomer of the macrocyclic cycloalkene is formed in all cases. The substrates for RCM can be obtained either via a Stille cross-coupling reaction of tributylvinylstannane or, even more efficiently, by Reck reactions of the aryl triflate precursors with pressurized ethene. Furthermore, the synthesis of 1 via RCM is compared with an alternative approach employing a low-valent titanium-induced McMurry coupling of dialdehyde 47 for the formation of the large ring. This direct comparison clearly ends in favor ofmetathesis which turned out to be superior in all preparatively relevant respects.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/04/20 alle ore 00:33:23