Total Synthesis of Dixiamycins A and B via a Late-Stage N-N Bond Formation under Visible Light Photoredox Catalysis

被引：0

作者：

Nandi, Rhituparna ^{[1
]}

Murmu, Ranjit ^{[2
]}

Sadhukhan, Sreyashi ^{[2
]}

Pal, Debopam ^{[2
]}

Biswas, Souvik ^{[2
]}

Das, Bishnu ^{[2
]}

Bisai, Alakesh ^{[1
,2
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, Madhya Pradesh, India

[2] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741246, W Bengal, India

来源：

ORGANIC LETTERS | 2025年 / 27卷 / 06期

关键词：

DERIVATIVES; ORIDAMYCIN; CARBAZOLE; XIAMYCIN; ACID;

D O I：

10.1021/acs.orglett.5c00083

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intermolecular oxidative N-N bond formation reactions are quite challenging and are largely uncharted. N-N linked dimeric indolosesquiterpene alkaloids represent an underexplored class of natural products, and strategies for direct dehydrogenative N-N bond formation are limited. Here, we have reported that a late-stage visible-light photoredox catalysis facilitates N-N bond formation, leading to the total syntheses of atropo-diastereomers dixiamycins A (1a) and B (1b).

引用

页码：1531 / 1536

页数：6

共 50 条

[21] A Synthesis of 1H-Indazoles via a Cu(OAc)2-Catalyzed N-N Bond Formation
Chen, Cheng-yi
Tang, Guangrong
He, Fengxian
Wang, Zhaobin
Jing, Hailin
Faessler, Roger
ORGANIC LETTERS, 2016, 18 (07) : 1690 - 1693
[22] Visible light photoredox catalysis: conversion of a mixture of thiophenols and nitriles into 2-substituted benzothiazoles via consecutive C-S and C-N bond formation reactions
Natarajan, Palani
Muskan, Manjeet
Brar, Navpreet Kaur
Kaur, Jaskamal Jot
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (09): : 1527 - 1531
[23] Synthesis of 2-Substituted 1,2,3-Triazoles via an Intramolecular N-N Bond Formation
Chen, Cheng-yi
Lu, Xiaowei
Holland, Mareike C.
Lv, Shichang
Ji, Xuebao
Liu, Wei
Liu, Jie
Depre, Dominique
Westerduin, Pieter
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (05) : 548 - 551
[24] An Effective Method for the Synthesis of 1,3-Dihydro-2H-indazoles via N-N Bond Formation
Zhang, Xiaoke
Pan, Yang
Liang, Peng
Ma, Xiaofeng
Jiao, Wei
Shao, Huawu
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (24) : 5552 - 5557
[25] Copper-Catalyzed N-N Bond Formation by Homocoupling of Ketoximes via N-O Bond Cleavage: Facile, Mild, and Efficient Synthesis of Azines
Zhao, Mi-Na
Liang, Hao
Ren, Zhi-Hui
Guan, Zheng-Hui
SYNTHESIS-STUTTGART, 2012, 44 (10): : 1501 - 1506
[26] Catalyst-Free Visible Light-Induced N-N Bond Cleavage for the Synthesis of Iminophosphorane Using Triarylphosphine and N-Sulfonyl and N-Acylaminopyridinium Salt
Qin, Xiaotao
Yang, Chenglei
Xue, Yinjiang
Hu, Jinkai
Yang, Jinhui
Li, Dianjun
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (11)
[27] An efficient route to polynitrogen-fused tricycles via a nitrene-mediated N-N bond formation under microwave irradiation
Nyffenegger, Coralie
Pasquinet, Eric
Suzenet, Franck
Poullain, Didier
Jarry, Christian
Leger, Jean-Michel
Guillaumet, Gerald
TETRAHEDRON, 2008, 64 (40) : 9567 - 9573
[28] Metal-free visible-light-mediated organophotoredox catalysis: synthesis of 3-functionalized indole via C–C, C–N bond formation
Neetu Yadav
Mohd Danish Ansari
Vijay B. Yadav
Ankit Verma
Saurabh K. Tiwari
Saif Ansari
I. R. Siddiqui
Molecular Diversity, 2021, 25 : 1103 - 1109
[29] Total Synthesis of (+)-Muricatetrocin B via a Late-Stage Co-Catalyzed Hartung-Mukaiyama Cyclization
Minami, Riko
Kasai, Tsubasa
Murata, Keisuke
Fuwa, Haruhiko
ORGANIC LETTERS, 2023, 25 (31) : 5745 - 5749
[30] C-X (X=C, O, S, N, B, P) Bond Deuteration and Late-Stage Applications
Xu, Hui
Zhang, Yun-Qian
Dai, Hui-Xiong
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (48)

← 1 2 3 4 5 →