title: Synthesis of the 5,6-dihydroxymorpholin-3-one fragment of monanchocidin A.
abstract: Monanchocidin A is a recently isolated pentacyclic guanidinium alkaloid that contains an unusual highly oxidized morpholinone fragment. Herein we report a rapid synthesis of this heterocyclic scaffold and confirm its structure. The key reaction involves an acid promoted hemiketalization/hemiaminalization of an α-hydroxyamide and α-ketoaldehyde that proceeds with exclusive regioselectivity and high diastereoselectivity to form the natural scaffold in moderate to high yield.
authors: Department of Chemistry, North Carolina State University , Raleigh, North Carolina 27695, United States.
authors: Yunlong
authors: Y
authors: Shi
authors: Joshua G
authors: JG
authors: Pierce
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D019791:Guanidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000600189:5,6-dihydroxymorpholin-3-one; D000470:Alkaloids; D009025:Morpholines; C554301:monanchocidin; D019791:Guanidine