Total synthesis of (-)-hennoxazole A.
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]
Smith
Thomas E
TE
Department of Chemistry, Williams College, Williamstown, MA 01267, USA. tsmith@williams.edu
Kuo
Wen-Hsin
WH
Bock
Victoria D
VD
Roizen
Jennifer L
JL
Balskus
Emily P
EP
Theberge
Ashleigh B
AB
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
D000498:Allyl Compounds; D001688:Biological Products; D006842:Hydrocarbons, Brominated; D010080:Oxazoles; D011522:Protons; D011714:Pyrans; D053778:Thiazolidines; C108742:hennoxazole A; C033089:thiazoline-2-thione