Total Synthesis of (+)-Haperforin G

Total Synthesis of (+)-Haperforin G

A concise chemical synthesis of (+)-haperforin G in 20 steps from commercially available starting materials is achieved with the integration of the Co-catalyzed intramolecular Pauson–Khand reaction for the stereoselective construction of cyclopentanone bearing an all-carbon quaternary stereogenic ce...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 142; no. 46; pp. 19487 - 19492
Main Authors: Zhang, Wei, Zhang, Zhenyu, Tang, Jun-Chen, Che, Jin-Teng, Zhang, Hao-Yu, Chen, Jia-Hua, Yang, Zhen
Format: Journal Article
Language:English
Published: United States American Chemical Society 18-11-2020
Online Access:Get full text
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Summary:A concise chemical synthesis of (+)-haperforin G in 20 steps from commercially available starting materials is achieved with the integration of the Co-catalyzed intramolecular Pauson–Khand reaction for the stereoselective construction of cyclopentanone bearing an all-carbon quaternary stereogenic center at the bridge-head position and the light-initiated photocatalysis for convergent and asymmetric cross-coupling of the unstabilized C­(sp3)-radical with an enone. The developed chemistry paves the way to synthesizing structurally diverse analogs of haperforin G (6).
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c10122