The application of vinylogous iminium salt derivatives to efficient formal syntheses of the marine akaloids lamellarin G trimethyl ether and ningalin B.
Studies directed at the synthesis of lamellarin G trimethyl ether and ningalin B via vinylogous iminium salt derivatives are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole or a 1,2,3,4-tetrasubstituted pyrrole from a vinylogous iminium salt or vinylogous iminium salt derivative. Subsequent transformations of these highly substituted pyrroles lead to efficient and regiocontrolled formal syntheses of the respective pyrrole containing natural products.
Gupton
John T
JT
Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Giglio
Benjamin C
BC
Eaton
James E
JE
Rieck
Elizabeth A
EA
Smith
Kristin L
KL
Keough
Matthew J
MJ
Barelli
Peter J
PJ
Firich
Lauren T
LT
Hempel
Jonathan E
JE
Smith
Timothy M
TM
Kanters
Rene P F
RP