A General Carbazole Synthesis via Stitching of Indole–Ynones with Nitromethanes: Application to Total Synthesis of Carbazomycin A, Calothrixin B, and Staurosporinone

Organic Letters
2019.0

Abstract

A new, one-pot domino benzannulation reaction between indole-3-ynones and various nitromethane derivatives has been explored for a general entry to diversely functionalized carbazole frameworks (28 examples). The scope of this new benzannulation has been extended to variants like 2-chloroindole-3-ynones to eventuate in chemo-differentiated 1,2,3,4-tetrasubstituted carbazoles with retention of the nitro group. The efficacy of this strategy has been demonstrated through concise total synthesis of natural products, viz. carbazomycin A, calothrixin B, and staurosporinone (K252c).

Knowledge Graph

Similar Paper

A General Carbazole Synthesis via Stitching of Indole–Ynones with Nitromethanes: Application to Total Synthesis of Carbazomycin A, Calothrixin B, and Staurosporinone
Organic Letters 2019.0
Integrated synthesis of 3,4-carbazoquinone alkaloids N-Me-carbazoquinocin A, B and D–F
RSC Advances 2024.0
Indolocarbazoles.3. Synthesis of novel aza analogs of staurosporine and K 252a as PKC inhibitors.
Bioorganic & Medicinal Chemistry Letters 1994.0
Natural product leads for drug discovery: Isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents
Bioorganic & Medicinal Chemistry 2009.0
Natural product leads for drug discovery: Isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents
Bioorganic & Medicinal Chemistry 2009.0
Diversity Oriented Convergent Access for Collective Total Synthesis of Bioactive Multifunctional Carbazole Alkaloids: Synthesis of Carbazomycin A, Carbazomycin B, Hyellazole, Chlorohyellazole, and Clausenaline D
Organic Letters 2014.0
Construction of <i>N</i>-Heterocycles Fused with a Highly Substituted Benzene Ring by a Benzyne-Mediated Cyclization/Functionalization Cascade Reaction and Its Application to the Total Synthesis of Marine Natural Products
Chemical and Pharmaceutical Bulletin 2021.0
Total Synthesis of (+)‐Alstonlarsine A
Angewandte Chemie International Edition 2022.0
A highly efficient methodology for the preparation of N-methoxycarbazoles and the total synthesis of 3,3′-[oxybis(methylene)]bis(9-methoxy-9H-carbazole)
Frontiers of Chemical Science and Engineering 2021.0
Total synthesis of natural pyrano[3,2-a]carbazole alkaloids
Tetrahedron 2023.0