Total Synthesis of (-)-Xishacorene B from ( R)-Carvone Using a C-C Activation Strategy

Journal of the American Chemical Society
Isabel KerschgensRichmond Sarpong

Abstract

The activation of C-C bonds that are traditionally viewed as unreactive, when coupled with other bond-forming processes, can offer new approaches to the synthesis of complex molecular scaffolds. In this Communication, we demonstrate the conversion of carvone to unusual bicyclo[3.3.1] and [3.2.1] frameworks by exploiting a Pd(0)-catalyzed C-C bond activation reaction and a radical cyclization process. This sequence is applied to a 10-step synthesis of the diterpene xishacorene B.

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Citations

Sep 25, 2019·Chemistry, an Asian Journal·Shoji KobayashiAraki Masuyama
Oct 8, 2019·Chemical Communications : Chem Comm·Xuan YangJian-Bo Xie
Feb 7, 2020·Natural Product Reports·Anthony R CarrollMichèle R Prinsep
Oct 8, 2019·Chemical Science·Alexander R RoviraRichmond Sarpong
Jan 28, 2020·Angewandte Chemie·Brian WangRichmond Sarpong
Dec 15, 2020·Chemistry : a European Journal·Friederike RatschHans-Günther Schmalz
Mar 24, 2021·Journal of the American Chemical Society·Yuegang ChenZhiwei Zuo
Aug 20, 2020·Journal of the American Chemical Society·Guangpeng XuChao Li
Sep 24, 2020·Chemical Reviews·Masahiro Murakami, Naoki Ishida
Nov 19, 2020·The Journal of Organic Chemistry·Xianhuang ZengDale L Boger
Nov 24, 2021·Journal of the American Chemical Society·Kerry E JonesRichmond Sarpong
Jan 29, 2022·Organic & Biomolecular Chemistry·Monosij NandySamik Nanda

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