Synthesis of notoamide J: a potentially pivotal intermediate in the biosynthesis of several prenylated indole alkaloids.
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.
Finefield
Jennifer M
JM
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Williams
Robert M
RM
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
D026121:Indole Alkaloids; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C551124:notoamide J; C022960:2-oxindole; D014364:Tryptophan; D011392:Proline