title: A Highly Stereoselective and Scalable Synthesis of L-allo-Enduracididine.
abstract: A highly stereoselective and scalable synthesis of L-allo-enduracididine from hydroxyproline derivative is described. Pyrrolidine oxidation and reductive ring opening are the key steps in the synthesis. Compared to previously reported approaches, the current route affords l-allo-enduracididine in 10 steps from 3 in 31% overall yield with >50:1 diastereoselectivity.
authors.affiliation: Department of Chemistry, University of Central Florida , Orlando, Florida 32816, United States.
authors.forename: William
authors.initials: W
authors.lastname: Craig
authors.affiliation: Department of Chemistry, University of Central Florida , Orlando, Florida 32816, United States.
authors.forename: Janet
authors.initials: J
authors.lastname: Chen
authors.affiliation: Department of Chemistry, University of Central Florida , Orlando, Florida 32816, United States.
authors.forename: David
authors.initials: D
authors.lastname: Richardson
authors.affiliation: Department of Chemistry, University of Central Florida , Orlando, Florida 32816, United States.
authors.forename: Rondel
authors.initials: R
authors.lastname: Thorpe
authors.affiliation: Department of Chemistry, University of Central Florida , Orlando, Florida 32816, United States.
authors.forename: Yu
authors.initials: Y
authors.lastname: Yuan
mesh_terms: D006909:Hydroxyproline / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000409:Alanine / Q000031:analogs & derivatives
chemical_list: D006909:Hydroxyproline; D011759:Pyrrolidines; C000603877:L-allo-enduracididine; D000409:Alanine