Asymmetric total synthesis of alkaloids 223A and 6-epi-223A.
Concise and asymmetric total synthesis of the title compounds are described. The key ring system was constructed using an intramolecular Schmidt reaction on a norbornenone derivative, which was subsequently subjected to ring-opening metathesis followed by reduction. An unusual isomerization of the C-6 ethyl group afforded the desired stereochemistry of the natural product. The synthesis is readily adaptable to analogue production.
Ghosh
Partha
P
Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, University of Kansas, Lawrence, Kansas 66045-7582, USA.
Judd
Weston R
WR
Ribelin
Timothy
T
Aubé
Jeffrey
J
D000470:Alkaloids / Q000138:chemical synthesis*; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D054836:Indolizidines; D007769:Lactams