Regiocontrol in an intramolecular Schmidt reaction: total synthesis of (+)-aspidospermidine.
[reaction--see text] A total synthesis of (+)-aspidospermidine (1) is described, featuring an intramolecular Schmidt reaction as the key step. The effects of stereochemistry and protecting group status on the regio- and chemoselectivity of this reaction were examined.
Iyengar
R
R
Department of Medicinal Chemistry, The University of Kansas, Lawrence 66045-2506, USA.
Schildknegt
K
K
Aubé
J
J
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D026121:Indole Alkaloids; D007211:Indoles; D011804:Quinolines; D013095:Spermidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D026121:Indole Alkaloids; D007211:Indoles; D011804:Quinolines; C409672:aspidospermidine; D013095:Spermidine