Enantioselective Total Synthesis of (+)-Propolisbenzofuran B
Wen-Xiu Xu , Li-Han Zhao , Yao Zhu , Hai-Hua Lu
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (22) : 2833 -2839.
Enantioselective Total Synthesis of (+)-Propolisbenzofuran B
The first catalytic asymmetric total synthesis of (+)-propolisbenzofuran B, enabled by a highly enantioselective rhodium-catalyzed hydrogenation of a tetrasubstituted olefin, was described. Other noteworthy aspects include the construction of the central hydrodibenzo[ b, d]furan core through a sequence of Zn(II)-mediated regioselective benzofuran formation and Dieckmann condensation, as well as C-H oxidations, involving a visible light-induced Fe(III)-catalyzed benzylic C(sp 3)-H oxidation. Additionally, the absolute configuration was confirmed by X-ray analysis of a carbonate intermediate.
Propolisbenzofuran B / Total synthesis / Enantioselective hydrogenation / Photocatalysis / C—H functionalization / Natural products / Alkenes / Chirality
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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