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Bio-inspired synthesis of xishacorenes A, B, and C, and a new congener from fuscol

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Abstract

The xishacorene natural products are structurally unique apolar diterpenoids that feature a bicyclo[3.3.1] framework. These secondary metabolites likely arise from the well-studied, structurally related diterpenoid fuscol. In this manuscript, we describe the conversion of fuscol to xishacorenes A, B, and C, as well as a previously unreported congener, which we have named xishacorene D. In addition, we describe immunomodulatory activity studies of the xishacorenes, a structurally related analogue, and fuscol. These studies were aided by an accurate determination of the physical properties (e.g., molar extinction coefficient) of the highly apolar xishacorenes.

Graphical abstract: Bio-inspired synthesis of xishacorenes A, B, and C, and a new congener from fuscol

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Publication details

The article was received on 28 May 2019, accepted on 02 Jul 2019 and first published on 03 Jul 2019


Article type: Edge Article
DOI: 10.1039/C9SC02572C
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Bio-inspired synthesis of xishacorenes A, B, and C, and a new congener from fuscol

    A. R. Rovira, N. Müller, W. Deng, C. Ndubaku and R. Sarpong, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC02572C

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