First asymmetric total synthesis of (+)-sparteine.
[reaction: see text] The total synthesis of (+)-sparteine was accomplished from 2,5-norbornadione in 15 steps and 15.7% overall yield. The key steps were two ring-expansion reactions, one involving an intramolecular Schmidt reaction and one using a novel variant of the photo-Beckmann rearrangement.
Smith
Brenton T
BT
The University of Kansas, Department of Medicinal Chemistry, Malott Hall, 1251 Wescoe Hall Drive, Room 4070, Lawrence, Kansas 66045-7582, USA.
Wendt
John A
JA
Aubé
Jeffrey
J
D002317:Cardiovascular Agents / Q000138:chemical synthesis; D003500:Cyclization; D009636:Norbornanes / Q000737:chemistry; D013034:Sparteine / Q000138:chemical synthesis*; D013237:Stereoisomerism
D002317:Cardiovascular Agents; D009636:Norbornanes; D013034:Sparteine; C048294:2,5-norbornadiene