title: Synthesis of notoamide J: a potentially pivotal intermediate in the biosynthesis of several prenylated indole alkaloids.
abstract: An efficient total synthesis of notoamide J, a new prenylated indole alkaloid and potential biosynthetic precursor, is described herein. Starting from L-proline and a substituted tryptophan derivative, this synthesis also employs an oxidation and pinacol rearrangement for the formation of the oxindole in the final step.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Finefield
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
mesh_terms: D001230:Aspergillus / Q000378:metabolism; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D007211:Indoles / Q000138:chemical synthesis; D015394:Molecular Structure; D000078183:Oxindoles; D054876:Prenylation; D011392:Proline / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis; D014364:Tryptophan / Q000096:biosynthesis / Q000737:chemistry
chemical_list: D026121:Indole Alkaloids; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C551124:notoamide J; C022960:2-oxindole; D014364:Tryptophan; D011392:Proline