Concise, asymmetric total synthesis of spirotryprostatin A.
[structure: see text] The structurally intriguing cell-cycle inhibitor spirotryprostatin A has been synthesized utilizing an azomethine ylide dipolar cycloaddition reaction as the key step. This pentacyclic alkaloid contains a prenylated tryptophan-derived oxindole moiety that has been created in a regiocontrolled and stereocontrolled manner in a single step.
Onishi
Tomoyuki
T
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Sebahar
Paul R
PR
Williams
Robert M
RM
D001391:Azo Compounds / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives
D001391:Azo Compounds; D026121:Indole Alkaloids; D010879:Piperazines; D013141:Spiro Compounds; C478300:spirotryprostatin A; D014364:Tryptophan