title: Total synthesis of (-)-hennoxazole A.
abstract: An enantioselective, convergent, total synthesis of the antiviral marine natural product (-)-hennoxazole A has been completed in 17 steps, longest linear sequence, from serine methyl ester and in 9 steps from an achiral bisoxazole intermediate. Elaboration of a thiazolidinethione allowed for rapid assembly of the pyran-based ring system. Key late-stage coupling was effected by deprotonation of the bisoxazole methyl group, followed by alkylation with an allylic bromide side chain segment. [structure: see text]
authors.affiliation: Department of Chemistry, Williams College, Williamstown, MA 01267, USA. tsmith@williams.edu
authors.forename: Thomas E
authors.initials: TE
authors.lastname: Smith
authors.forename: Wen-Hsin
authors.initials: WH
authors.lastname: Kuo
authors.forename: Victoria D
authors.initials: VD
authors.lastname: Bock
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Roizen
authors.forename: Emily P
authors.initials: EP
authors.lastname: Balskus
authors.forename: Ashleigh B
authors.initials: AB
authors.lastname: Theberge
mesh_terms: D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D008956:Models, Chemical; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011522:Protons; D011714:Pyrans / Q000737:chemistry; D013237:Stereoisomerism; D053778:Thiazolidines / Q000737:chemistry
chemical_list: D000498:Allyl Compounds; D001688:Biological Products; D006842:Hydrocarbons, Brominated; D010080:Oxazoles; D011522:Protons; D011714:Pyrans; D053778:Thiazolidines; C108742:hennoxazole A; C033089:thiazoline-2-thione