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Total Synthesis of the Pyranoisoflavone Kraussianone 1 and Related Isoflavones

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School of Chemistry, University of KwaZulu-Natal, Private Bag X01, Scottsville 3209, Pietermaritzburg, South Africa
* To whom correspondence should be addressed. Tel: +27 33 2605886. Fax: +27 33 2605009. E-mail: [email protected]
Cite this: J. Nat. Prod. 2010, 73, 10, 1680–1685
Publication Date (Web):August 18, 2010
https://doi.org/10.1021/np100407n
Copyright © 2010 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    The first total synthesis of the pyranoisoflavone kraussianone 1 (1) is described. The key steps involved the Suzuki−Miyaura reaction for the construction of the isoflavone core and the regioselective formation of the dimethylpyran scaffolds to the phloroglucinol (ring A) and resorcinol (ring B) moieties of kraussianone 1 (1). This route also provided access to the related isoflavones eriosemaone D (2) and genistein (3) via simple structural modifications.

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    Copies of NMR spectra of kraussianone 1 (1), eriosemaone D (2), genistein (3), and synthetic intermediates 4, 5, 6, 10, 13, 18, 19, 20, and 23. This material is available free of charge via the Internet at http://pubs.acs.org.

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