Gold-catalyzed Cycloisomerization of N-Propargylindole-2-carboxamides: Application Toward the Synthesis of Lavendamycin Analogues

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2008 Jul 17

PMID 18627172

Citations 11

Authors

Dylan B England

Albert Padwa

Affiliations

Soon will be listed here.

Abstract

A series of N-propargylindole-2-carboxamides were found to undergo a AuCl 3-catalyzed cycloisomerization to give beta-carbolinones in high yield. The corresponding beta-chlorocarboline derivative was prepared and used for Pd(0)-catalyzed cross-coupling chemistry directed toward the synthesis of lavendamycin analogues.

Citing Articles

Morita-Baylis-Hillman reaction of 3-formyl-9-pyrido[3,4-]indoles and fluorescence studies of the products.

Devi N, Singh V Beilstein J Org Chem. 2022; 18:926-934.

PMID: 35957752 PMC: 9344545. DOI: 10.3762/bjoc.18.92.

A Direct and an Efficient Regioselective Synthesis of 1,2-Benzothiazine 1,1-dioxides, β-Carbolinones, Indolo[2,3-]pyran-1-ones, Indolo[3,2-]pyran-1-ones, Thieno[2,3-]pyran-7-ones and Pyrano[3',4':4,5]imidazo[1,2-]pyridin-1-ones via Tandem....

Jismy B, Cherry K, Maaliki C, Inack Ngi S, Abarbri M Molecules. 2020; 25(21).

PMID: 33158260 PMC: 7663652. DOI: 10.3390/molecules25215137.

Synthesis of 2,3-Disubstituted 4-Ethoxycarbonyl-β-carbolin-1-ones: Application to the Synthesis of SL651498 and Its Analogue.

Miura R, Goto S, Hashimoto T, Hachiya I ACS Omega. 2020; 5(25):15631-15656.

PMID: 32637839 PMC: 7331213. DOI: 10.1021/acsomega.0c01854.

β-Carbolinone Analogues from the Ugi Silver Mine.

Madhavachary R, Naveen N, Wang Y, Wang Q, Konstantinidou M, Domling A European J Org Chem. 2019; 2018(24):3139-3143.

PMID: 31440115 PMC: 6706090. DOI: 10.1002/ejoc.201800557.

Pd(OAc)2-catalyzed dehydrogenative C-H activation: An expedient synthesis of uracil-annulated β-carbolinones.

Mondal B, Hazra S, Panda T, Roy B Beilstein J Org Chem. 2015; 11:1360-6.

PMID: 26425190 PMC: 4578345. DOI: 10.3762/bjoc.11.146.