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  Total Syntheses of (S)-(−)-Zearalenone and Lasiodiplodin Reveal Superior Metathesis Activity of Ruthenium Carbene Complexes with Imidazol-2-ylidene Ligands

Fürstner, A., Thiel, O. R., Kindler, N., & Bartkowska, B. (2000). Total Syntheses of (S)-(−)-Zearalenone and Lasiodiplodin Reveal Superior Metathesis Activity of Ruthenium Carbene Complexes with Imidazol-2-ylidene Ligands. The Journal of Organic Chemistry, 65(23), 7990-7995. doi:10.1021/jo0009999.

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Fürstner, Alois1, Author              
Thiel, Oliver R.1, Author              
Kindler, Nicole1, Author              
Bartkowska, Beata2, Author
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1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Krüger (XRAY), Max-Planck-Institut für Kohlenforschung, Max Planck Society, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, DE, ou_1445624              

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 Abstract: Total syntheses of the bioactive orsellinic acid derivatives zearalenone 3 and 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 Heck 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 of metathesis which turned out to be superior in all preparatively relevant respects.

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Language(s): eng - English
 Dates: 2000-07-032000-10-212000-11-17
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jo0009999
 Degree: -

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Title: The Journal of Organic Chemistry
  Other : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: 6 Volume / Issue: 65 (23) Sequence Number: - Start / End Page: 7990 - 7995 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1