First stereo selective synthesis of 5-O-feruloyl-2-deoxy-d-ribono-γ-lactone

• Published in: Tetrahedron letters Vol. 57; no. 42; pp. 4734 - 4736
• Main Authors: Ganesh, K. Ravi, Rao, K. Raghavendra, Pratap, T.V., Raghunadh, A., Kumar, S. Praveen, Basaveswara Rao, M.V., Murthy, C., Meruva, Suresh Babu
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 19.10.2016; Elsevier
• Subjects: 2-Deoxy-d-ribono-γ-lactone; 5-O-Feruloyl-2-deoxy-d-ribono-γ-lactone; Chemistry; Chemistry, Organic; Ferulic acid; O-PMB deprotection; Physical Sciences; Science & Technology; trans-Cinnamic acid; 2-Deoxy-d-ribono-γ-lactone; 5-O-Feruloyl-2-deoxy-d-ribono-γ-lactone; O-PMB deprotection; trans-Cinnamic acid; Ferulic acid; VITTARIA-ANGUSTE-ELONGATA; 2-Deoxy-D-ribono-gamma-lactone; 5-O-Feruloyl-2-deoxy-D-ribono-gamma-lactone; STEREOSELECTIVE-SYNTHESIS; DEPROTECTION; O-FMB deprotection
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2016.09.041

[Display omitted] •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 CeCl3·7H2O and NaI. 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.