Revisiting a classic approach to the Aspidosperma alkaloids: an intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine.
[reaction: see text] A total synthesis of (+)-aspidospermidine (1) is described. The key reactions used in the synthesis of this pentacyclic Aspidosperma alkaloid were a deracemizing imine alkylation/Robinson annulation sequence, a selective "redox ketalization", and an intramolecular Schmidt reaction. A Fischer indolization step carried out on a tricyclic ketone mirrored the sequence reported by Stork and Dolfini in their classic aspidospermine synthesis.
Iyengar
Rajesh
R
Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Room 4070, Malott Hall, University of Kansas, Lawrence, Kansas 66045-7582, USA.
Schildknegt
Klaas
K
Morton
Martha
M
Aubé
Jeffrey
J
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D030009:Aspidosperma / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D026121:Indole Alkaloids; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D001386:Azides; D026121:Indole Alkaloids; D007211:Indoles; D007659:Ketones; D011804:Quinolines; C409672:aspidospermidine