A monocyclic neodysiherbaine analog: Synthesis and evaluation. Issue 21 (1st November 2016)

• Record Type: Journal Article
• Authors: Fukushima, Koichi; Ishikawa, Yuichi; Sakai, Ryuichi; Oikawa, Masato
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 26:Issue 21(2016)
• Page Start: 5164
• Page End: 5167
• Publication Date: 2016-11-01
• Subjects: Neodysiherbaine -- Natural product analog -- Stereoselective synthesis -- Domino reaction -- Aldol reaction -- Dihydroxylation -- Excitatory amino acid -- Neuroactivity; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2016.09.074
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: Monocyclic analog of neuroexcitatory neodysiherbaine has been designed and stereoselectively synthesized in 0.40% yield over total 24 steps starting fromd -ribose, by employing domino aldol-Cannizzaro reaction and stereoselective aldol reaction for construction of two quaternary carbon stereogenic centers at C4 and C6 positions, respectively. The hyperactivity of neodysiherbaine in mice was found to deteriorate in the novel analog, upon intracerebroventricular injection.