Asymmetric Synthesis of cis- and trans-2-Aryl-6-methylpyrans from D-Glucose by Arylation and Inversion of Configuration at the C-2 Position

作者：Michigami Kyosuke; Shimazaki Atsuko; Hayashi Masahiko^*

来源：European Journal of Organic Chemistry, 2014, 2014(1): 244-253.

DOI：10.1002/ejoc.201301376

• Carbohydrates
• Asymmetric synthesis
• Medicinal chemistry
• Oxygen heterocycles
• Arylation
• Deoxygenation
• Chiral pool

Asymmetric synthesis of optically active cis- and trans-2-aryl-6-methylpyrans from commercially available tetra-O-acetyl-D-glucopyranosyl bromide has been developed. The reaction proceeds by two important steps. One is the arylation, and the other is deoxygenation at the C-3 position and inversion of configuration at the C-2 position during the preparation of the cis-isomer, when 2-aryl-3-hydroxy-6-(hydroxymethyl)pyrans were treated with trimethylsilyl chloride and sodium iodide.

• 出版日期2014-1