First stereo selective synthesis of 5-O-feruloyl-2-deoxy-d-ribono-γ-lactone. Issue 42 (19th October 2016)

• Record Type: Journal Article
• Authors: Ganesh, K. Ravi; Rao, K. Raghavendra; Pratap, T.V.; Raghunadh, A.; Kumar, S. Praveen; Basaveswara Rao, M.V.; Murthy, C.; Meruva, Suresh Babu
• Is Part Of: Tetrahedron letters. Volume 57:Issue 42(2016)
• Page Start: 4734
• Page End: 4736
• Publication Date: 2016-10-19
• Subjects: trans-Cinnamic acid -- Ferulic acid -- 2-Deoxy-d-ribono-γ-lactone -- O-PMB deprotection -- 5-O-Feruloyl-2-deoxy-d-ribono-γ-lactone; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.09.041
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Established first total synthesis of 5- O -feruloyl-2-deoxy-d -ribono-γ-lactone. The synthesis began with economically benign protected ( R )-glyceraldehyde. The unreported O -PMB protected intermediates were synthesized. Employed Pinnick conditions for oxidation of terminal aldehyde. Optimized the O -PMB deprotection conditions and succeeded using CeCl3 ·7H2 O and NaI. Abstract: The first stereo selective synthesis of 5- O -feruloyl-2-deoxy-d -ribono-γ-lactone was achieved by coupling reaction of substituted ferulic acid and hydroxy methyl ribono lactone and followed by deprotection of O -PMB. The spectroscopic data were compared with the reported values and a clear indication to the absolute stereochemistry of the natural 5- O -feruloyl-2-deoxy-d -ribono-γ-lactone.