Total synthesis of (+/-)-aspidospermidine.
(+/-)-Aspidospermidine (1) has been synthesized from readily available methyl 3-ethyl-2-oxocylo-pentanecarboxylate (17) in 5.9% yield over 13 steps. The key step of the synthesis is an intramolecular cascade reaction that simultaneously forms the B, C, and D rings of 1. A high-yielding method of closing the remaining E ring is also described.
Toczko
M A
MA
Department of Chemistry, University of California, Berkeley 94720, USA.
Heathcock
C H
CH
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D026121:Indole Alkaloids; D007211:Indoles; D015394:Molecular Structure; D011804:Quinolines
D000470:Alkaloids; D026121:Indole Alkaloids; D007211:Indoles; D011804:Quinolines; C409672:aspidospermidine