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Synthesis 2016; 48(01): 150-160
DOI: 10.1055/s-0035-1560359
DOI: 10.1055/s-0035-1560359
paper
Synthesis of the Pyrano[3,2-a]carbazole Alkaloids Koenine, Koenimbine, Koenigine, Koenigicine, and Structural Reassignment of Mukonicine
Further Information
Publication History
Received: 30 September 2015
Accepted: 01 October 2015
Publication Date:
08 October 2015 (online)
Abstract
Using the palladium(II)-catalyzed oxidative cyclization of a diarylamine and the annulation of a dimethylpyran ring by Lewis acid promoted reaction with prenal as key steps, the total syntheses of the 6-oxygenated pyrano[3,2-a]carbazole alkaloids koenine and koenimbine, and of the 6,7-dioxygenated pyrano[3,2-a]carbazole alkaloids koenigine and koenigicine (koenimbidine, koenidine) were achieved. Moreover, these studies led to an improved synthetic route to the 2,6-dioxygenated carbazole alkaloid glycozolidol. Mukonicine, originally published as 6,8-dimethoxypyrano[3,2-a]carbazole, was found to be identical with koenigicine.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560359.
- Supporting Information
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Isolation of girinimbine (1):
Reviews:
Recent applications:
For the isolation of glycozolidol (9), see:
For a previous total synthesis of glycozolidol (9), see ref. 17. For previous partial syntheses of glycozolidol (9), see:
For previous syntheses of koenigicine (4b), see: