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Synthesis of Indole-, Benzo[ b]thiophene-, and Benzo[ b]selenophene-Based Analogues of the Resveratrol Dimers Viniferifuran and (±)-Dehydroampelopsin B.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.ORCID iD: 0000-0002-3219-4669
2018 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 20, no 21, p. 6650-6654Article in journal (Refereed) Published
Abstract [en]

A convenient synthetic strategy to obtain viniferifuran and (±)-dehydroampelopsin B analogues based on the heterocyclic cores of indole, benzo[ b]thiophene, and benzo[ b]selenophene is presented. The key transformations utilized in the described syntheses include Sonogashira couplings, Cacchi and alkyne electrophilic cyclizations, Horner-Wadsworth-Emmons (HWE) reaction, chemoselective Suzuki-Miyaura couplings, and acid-promoted intramolecular cyclization to form the seven-membered ring of (±)-dehydroampelopsin B.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2018. Vol. 20, no 21, p. 6650-6654
National Category
Natural Sciences Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-153480DOI: 10.1021/acs.orglett.8b02638ISI: 000449443100009PubMedID: 30350667OAI: oai:DiVA.org:umu-153480DiVA, id: diva2:1265010
Funder
Swedish Research Council, 621-2014-4670Available from: 2018-11-21 Created: 2018-11-21 Last updated: 2018-11-27Bibliographically approved

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Saleeb, MichaelElofsson, Mikael

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