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Synthesis 2019; 51(24): 4635-4644
DOI: 10.1055/s-0037-1610729
DOI: 10.1055/s-0037-1610729
paper
Divergent Synthesis of Various 2-Aryl Iminocyclitols from (R)-p-Hydroxyphenylglycine
Further Information
Publication History
Received: 05 July 2019
Accepted after revision: 02 September 2019
Publication Date:
30 September 2019 (online)
Abstract
A concise and efficient synthesis of various 2-aryl iminocyclitols is reported from (R)-p-hydroxyphenylglycine using Upjohn dihydroxylation and base-promoted intramolecular cyclization. These 2-aryl iminocyclitols are the important structural framework of various bioactive compounds and also known as glycosidase inhibitors.
Keywords
Upjohn dihydroxylation - alkaloids - iminocyclitols - diastereoselectivity - glycosidase inhibitorSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610729.
- Supporting Information
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- 9 (R)-4-Hydroxyphenylglycine was first subjected to esterification followed by in situ Boc protection then phenolic O-methylation using K2CO3 and MeI. The ester was further reduced into an alcohol using LiAlH4 and later oxidized into an aldehyde using IBX. Wittig reaction of this aldehyde with Ph3P=CHCOOEt yielded olefin 6 in 59% yield overall.