4.8 Article

Toward Naphthocyclinones: Doubly Connected Octaketide Dimers with a Bicyclo[3.2.1]octadienone Core by Thiolate-Mediated Cyclization

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 33, Pages 9650-9653

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201503442

Keywords

cyclization; dimerization; dithiol reagents; quinones; synthetic methods

Funding

  1. JSPS [23000006]
  2. Grants-in-Aid for Scientific Research [23000006] Funding Source: KAKEN

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A viable method is reported for the synthesis of the bicyclo[3.2.1]octadienone scaffold in naturally occurring octaketide dimers. The procedure employs a reductive cyclization reaction mediated by an unusual ethanedithiol monosodium salt.

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