Gold Catalysis: Regio- and Stereoselective Total Synthesis of Xyloketals D and G and the Related Natural Product Alboatrin

A new and efficient one-pot desilylation–gold-catalyzed cycloisomerization of alkynes containing a silyl-protected phenolic −OH and a free alcoholic −OH unit leads selectively to the formation of tetrahydrofuranobenzopyran ring system. This approach has been used for the regio- and stereoselective s...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-03, Vol.78 (6), p.2413-2421
Main Authors: Panda, Biswajit, Sarkar, Tarun K
Format: Article
Language:English
Subjects:
Catalysis
Gold - chemistry
Molecular Structure
Pyrans - chemical synthesis
Pyrans - chemistry
Quinones - chemical synthesis
Quinones - chemistry
Stereoisomerism
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Summary:A new and efficient one-pot desilylation–gold-catalyzed cycloisomerization of alkynes containing a silyl-protected phenolic −OH and a free alcoholic −OH unit leads selectively to the formation of tetrahydrofuranobenzopyran ring system. This approach has been used for the regio- and stereoselective synthesis of xyloketal D, xyloketal G, and the related natural product alboatrin.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo302545n