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Synthesis of (±)-thiohalenaquinone by iterative metalations of thiophene

Wakefield, B and Halter, RJ and Wipf, P (2007) Synthesis of (±)-thiohalenaquinone by iterative metalations of thiophene. Organic Letters, 9 (16). 3121 - 3124. ISSN 1523-7060

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The synthesis of a thiophene-containing analogue of halenaquinone was realized. Key steps include an alkynyl ketone-benzocyclobutane Diels-Alder reaction to construct the C,D-ring naphthalene subunit, a Heck cyclization to form the quaternary carbon, and a ring closing metathesis to add the A-ring. © 2007 American Chemical Society.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Wakefield, B
Halter, RJ
Wipf, Ppwipf@pitt.eduPWIPF
Date: 2 August 2007
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 9
Number: 16
Page Range: 3121 - 3124
DOI or Unique Handle: 10.1021/ol071258y
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Animals; Cyclization; Molecular Structure; Porifera--chemistry; Quinones--chemical synthesis; Quinones--chemistry; Stereoisomerism; Thiophenes--chemistry
PubMed ID: 17630756
Date Deposited: 09 Oct 2013 16:04
Last Modified: 02 Feb 2019 15:56


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