Scalable Total Synthesis of (-)-Triptonide: Serendipitous Discovery of a Visible-Light-Promoted Olefin Coupling Initiated by Metal-Catalyzed Hydrogen Atom Transfer (MHAT)

Xianhe Fang; Nan Zhang; Si-Cong Chen; Tuoping Luo

doi:10.1021/jacs.1c12525

Scalable Total Synthesis of (-)-Triptonide: Serendipitous Discovery of a Visible-Light-Promoted Olefin Coupling Initiated by Metal-Catalyzed Hydrogen Atom Transfer (MHAT)

J Am Chem Soc. 2022 Feb 9;144(5):2292-2300. doi: 10.1021/jacs.1c12525. Epub 2022 Jan 28.

Authors

Xianhe Fang^{1

2}, Nan Zhang¹, Si-Cong Chen³, Tuoping Luo^{1

3

2}

Affiliations

¹ Peking-Tsinghua Center for Life Sciences, Academy for Advanced Interdisciplinary Studies, Peking University, Beijing 100871, China.
² Institute of Molecular Physiology, Shenzhen Bay Laboratory, Shenzhen, Guangdong 518055, China.
³ Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.

PMID: 35089705
DOI: 10.1021/jacs.1c12525

Abstract

An efficient and scalable total synthesis of (-)-triptonide is accomplished based on a metal-catalyzed hydrogen atom transfer (MHAT)-initiated radical cyclization. During the optimization of the key step, we discovered that blue LEDs significantly promoted the efficiency of reaction initiated by Co(TPP)-catalyzed MHAT. Further exploration and optimization of this catalytic system led to development of a dehydrogenative MHAT-initiated Giese reaction.

Publication types

Research Support, Non-U.S. Gov't