The Application of Vinylogous Iminium Salt Derivatives and Microwave Accelerated Vilsmeier-Haack Reactions to Efficient Relay Syntheses of the Polycitone and Storniamide Natural Products.
Studies directed at the synthesis of polycitone and storniamide natural products via vinylogous iminium salts and microwave accelerated Vilsmeier-Haack formylations are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole or a 2,3,4-trisubstituted pyrrole from a vinamidinium salt or vinamidinium salt derivative followed by formylation at the 5-position of the pyrrole. Subsequent transformations of the selectively formylated pyrroles lead to efficient and regiocontrolled relay syntheses of the respective pyrrole containing natural products.
Gupton
John T
JT
Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Banner
Edith J
EJ
Sartin
Melissa D
MD
Coppock
Matthew B
MB
Hempel
Jonathan E
JE
Kharlamova
Anastasia
A
Fisher
Daniel C
DC
Giglio
Ben C
BC
Smith
Kristin L
KL
Keough
Matt J
MJ
Smith
Timothy M
TM
Kanters
Rene P F
RP
Dominey
Raymond N
RN
Sikorski
James A
JA