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The Total Syntheses of Guttiferone A and 6-epi-Guttiferone A

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Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, DE-70569 Stuttgart, Germany
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Cite this: J. Am. Chem. Soc. 2014, 136, 10, 4026–4030
Publication Date (Web):February 22, 2014
https://doi.org/10.1021/ja500063a
Copyright © 2014 American Chemical Society
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    Abstract

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    Polyprenylated polycyclic acylphloroglucinols (PPAP) are a constantly growing class of natural products that exhibit a common bicyclo[3.3.1]nonatrione core and consist of currently more than 200 members. A subclassification among the various natural products of this class includes the position of the exocyclic acyl group, the prenylation grade of the core, and the relative configuration at C-7 within the core. About 10% of the reported structures, however, possess an additional chiral center at C-6. Herein we describe a straightforward access to guttiferone A and epi-guttiferone A, in which full control of stereoselectivity is achieved via conformational control, and a strict separation of framework decorating from framework constructing operations sets the stage for a short 13-step synthesis.

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