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Synthesis 2017; 49(06): 1190-1205
DOI: 10.1055/s-0036-1588939
DOI: 10.1055/s-0036-1588939
feature
Synthesis of Benzodioxane and Benzofuran Scaffolds Found in Neolignans via TMS Triflate Mediated Addition to 1,4-Benzodioxane Hemiacetals
Further Information
Publication History
Received: 09 December 2016
Accepted after revision: 23 December 2016
Publication Date:
17 January 2017 (online)
Abstract
This research reports the successful asymmetric synthesis of both a 9-hydroxy-5′-methoxy-1,4-benzodioxane framework and a highly functionalised benzofuran scaffold. Both synthetically desirable structures are the result of a Lewis acid catalysed addition of an aryl nucleophile to 1,4-benzodioxane hemiacetals and offer a route towards the synthesis of a number of naturally occurring neolignans.
Key words
lignin - 1,4-benzodioxane - benzofuran - asymmetric synthesis - hemiacetal - oxonium - Mitsunobu reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588939.
- Supporting Information
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