The First Synthesis of the ABC-Ring
System of ‘Upenamide
Jan Peter Schmidt
Sandra Beltrán-Rodil
Rhona J. Cox
Graeme D. McAllister
Mark Reid
Richard J. K. Taylor
10.1021/ol701772d.s002
https://acs.figshare.com/articles/journal_contribution/The_First_Synthesis_of_the_ABC_Ring_System_of_Upenamide/2983858
The first synthetic route to the spirooxaquinolizidinone core (ABC core) of the macrocyclic marine alkaloid ‘upenamide (<b>1</b>) has been developed.
All five stereocenters were introduced with complete stereocontrol. The hydroxyl group at C-11 was introduced by a regio- and stereoselective
SeO<sub>2</sub>-mediated allylic oxidation. The spirocyclic skeleton was formed by a stannous chloride induced deacetalization−bicyclization procedure.
Further stereocenters were introduced by an enzymatic desymmetrization and by incorporation of an (<i>S</i>)-malic acid derived building block.
2007-09-27 00:00:00
alkaloid
stereoselective
stereocenter
upenamide
acid
building block
desymmetrization
allylic
ABC core
spirooxaquinolizidinone core
hydroxyl group
stannous chloride
First Synthesis
oxidation
spirocyclic skeleton
regio
incorporation
SeO
marine
stereocontrol
UpenamideThe
macrocyclic
deacetalization
procedure