title: Synthesis and bioconversions of notoamide T: a biosynthetic precursor to stephacidin A and notoamide B.
abstract: In an effort to further elucidate the biogenesis of the stephacidin and notoamide families of natural products, notoamide T has been identified as the likely precursor to stephacidin A. The total synthesis of notoamide T is described along with it is C-6-epimer, 6-epi-notoamide T. The chemical conversion of stephacidin A to notoamide T by reductive ring opening is described as well as the oxidative conversion of notoamide T to stephacidin A. Furthermore, [(13)C](2)-notoamide T was synthesized and provided to Aspergillus versicolor and Aspergillus sp. MF297-2, in which significant incorporation was observed in the advanced metabolite, notoamide B.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: James D
authors.initials: JD
authors.lastname: Sunderhaus
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: McAfoos
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Finefield
authors.forename: Hikaru
authors.initials: H
authors.lastname: Kato
authors.forename: Shengying
authors.initials: S
authors.lastname: Li
authors.forename: Sachiko
authors.initials: S
authors.lastname: Tsukamoto
authors.forename: David H
authors.initials: DH
authors.lastname: Sherman
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
mesh_terms: D001230:Aspergillus / Q000235:genetics / Q000378:metabolism*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D026121:Indole Alkaloids; C520596:notoamide B; C470895:stephacidin A