Total Synthesis of (+/-)-Gelsemine.
A complex molecular reorganization (1-->2), a sequential anionic aza-Cope rearrangement and Mannich cyclization, and an unprecedented intramolecular Heck reaction of the tetrasubstituted double bond of a vinylogous carbamate are key steps in a new total synthesis of (+/-)-gelsemine (3). MOM=methoxymethyl, DBU=1,8-diazabicyclo[5.4.0]undec-7-ene.
Madin
A
Department of Chemistry, University of California, 516 Rowland Hall, Irvine, CA 92697-2025 (USA).
O'Donnell
CJ
Oh
T
Old
DW
Overman
LE
Sharp
MJ