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Synthesis of Indole-, Benzo[ B]thiophene-, and Benzo[ b]selenophene-Based Analogues of the Resveratrol Dimers Viniferifuran and (±)-Dehydroampelopsin B

Adrian Krzyzanowski, Michael Saleeb, Mikael Elofsson

Org Lett. 2018 Nov 2;20(21):6650-6654.

PMID: 30350667

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP113893086 Benzo[b]thien-3-ylboronic acid Benzo[b]thien-3-ylboronic acid 113893-08-6 Price
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