A short synthesis of protected 3-deoxy-D-arabino-2-heptulosonates (DAH) from shikimic acid based on silyl group migration

Abstract

The reaction of (2S,3S,4R)-2,3,4,7-tetrahydroxy-6-oxoheptanals with lower alcohols produced protected 3-deoxy-D-arabino-2-heptulosonates. The key transformation is based on an 1,4-O-O silyl group migration, followed by 6-exo-trig cyclisation to give the final pyranose. (C) 2018 Elsevier Ltd.

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Keywords

• Oxoheptanals
• Heptulosonates
• Silyl group migration
• Shikimic acid