title: Improved biomimetic total synthesis of D,L-stephacidin A.
abstract: The direct conversion of beta-hydroxyproline derivatives into 5-hydroxypyrazin-2(1H)-ones under Mitsunobu conditions has been discovered to be a general biomimetic protocol generating IMDA intermediates and has been applied to the concise, biomimetic total syntheses of D,L-stephacidin A and D,L-brevianamide B.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, USA.
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Greshock
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
mesh_terms: D006909:Hydroxyproline / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011719:Pyrazines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; D011719:Pyrazines; C470895:stephacidin A; D006909:Hydroxyproline