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

被引：33

作者：

Fang, Xianhe ^{[1
,2
]}

Zhang, Nan ^{[1
]}

Chen, Si-Cong ^{[3
,4
]}

Luo, Tuoping ^{[1
,2
,3
,4
]}

机构：

[1] Peking Univ, Acad Adv Interdisciplinary Studies, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China

[2] Inst Mol Physiol, Shenzhen Bay Lab, Shenzhen 518055, Guangdong, Peoples R China

[3] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China

[4] Peking Univ, Beijing Natl Lab Mol Sci, Coll Chem & Mol Engn, Beijing 100871, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2022年 / 144卷 / 05期

基金：

美国国家科学基金会;

关键词：

FORMAL TOTAL-SYNTHESIS; CENTER-DOT TRANSFER; RADICAL CYCLIZATIONS; COBALT; TRIPTOLIDE; BOND; TRIPTONIDE; PORPHYRINS; ALCOHOLS; REGIOSELECTIVITY;

D O I：

10.1021/jacs.1c12525

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：2292 / 2300

页数：9

共 119 条

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