title: A concise asymmetric total synthesis of (+)-brevisamide.
abstract: A new protecting-group-free synthesis of the marine monocyclic ether (+)-brevisamide is reported. The enantioselective synthesis utilizes a key asymmetric Henry reaction and an Achmatowicz rearrangement for the formation of the tetrahydropyran ring. A penultimate Stille cross-coupling allows for an efficient installation of the conjugated (E,E)-diene side chain ultimately delivering (+)-brevisamide.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, California 93106, USA.
authors.forename: Aaron T
authors.initials: AT
authors.lastname: Herrmann
authors.forename: Steven R
authors.initials: SR
authors.lastname: Martinez
authors.forename: Armen
authors.initials: A
authors.lastname: Zakarian
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D000470:Alkaloids; D011714:Pyrans; C532303:brevisamide; D000095702:Polyether Toxins