Bio-inspired synthesis of xishacorenes A, B, and C, and a new congener from fuscol. Issue 33 (10th July 2019)

• Record Type: Journal Article
• Authors: Rovira, Alexander R.; Müller, Nicolas; Deng, Weiwen; Ndubaku, Chudi; Sarpong, Richmond
• Is Part Of: Chemical science. Volume 10:Issue 33(2019)
• Page Start: 7788
• Page End: 7791
• Publication Date: 2019-07-10
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9sc02572c
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : In this manuscript, we describe the conversion of fuscol, a natural product isolated in 1978, to xishacorenes A, B, and C, isolated in 2017, as well as a previously unreported congener, which we have named xishacorene D. 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.