A short synthesis of protected 3-deoxy-d-arabino-2-heptulosonates (DAH) from shikimic acid based on silyl group migration. Issue 52 (26th December 2018)

• Record Type: Journal Article
• Authors: Gonda, Jozef; Psotka, Miroslav; Martinková, Miroslava; Fazekašová, Simona; Mitríková, Tatiana; Vilková, Mária
• Is Part Of: Tetrahedron letters. Volume 59:Issue 52(2018)
• Page Start: 4620
• Page End: 4621
• Publication Date: 2018-12-26
• Subjects: Oxoheptanals -- Heptulosonates -- Silyl group migration -- Shikimic acid; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.11.045
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A convenient approach to DHA derivatives from shikimic acid was developed. The 1, 4- O–O silyl group migration followed by cyclization gave the pyranose core. The configuration of the final heptulosonates was confirmed by NOESY experiments. Abstract: The reaction of (2 S, 3 S, 4 R )-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.