Issue 30, 2022

Total synthesis of (±)-vinoxine: construction of the bridged pyrido[1,2-a]indole skeleton via Tf2O-mediated Bischler–Napieralski reaction and stereoselective radical cyclization

Abstract

The total synthesis of (±)-vinoxine was achieved featuring the assembly of a multi-substituted tetrahydropyrido[1,2-a]indole skeleton through the Tf2O-mediated Bischler–Napieralski reaction. The characteristic diazabicyclo[3.3.1]nonane skeleton was stereoselectively constructed via radical cyclization based on the one stereochemistry of the C3 position. The established methodology provides new options for the synthesis of natural products and pharmaceuticals containing the multi-substituted pyrido[1,2-a]indole skeleton.

Graphical abstract: Total synthesis of (±)-vinoxine: construction of the bridged pyrido[1,2-a]indole skeleton via Tf2O-mediated Bischler–Napieralski reaction and stereoselective radical cyclization

  • This article is part of the themed collection: New Talent

Supplementary files

Article information

Article type
Communication
Submitted
09 feb. 2022
Accepted
03 mar. 2022
First published
03 mar. 2022

Org. Biomol. Chem., 2022,20, 5943-5947

Total synthesis of (±)-vinoxine: construction of the bridged pyrido[1,2-a]indole skeleton via Tf2O-mediated Bischler–Napieralski reaction and stereoselective radical cyclization

K. Okada, H. Ueda and H. Tokuyama, Org. Biomol. Chem., 2022, 20, 5943 DOI: 10.1039/D2OB00274D

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