Extending Pummerer reaction chemistry: application to the assembly of the pentacyclic core of dibromopalau'amine.
A pentacyclic model system featuring the trans azabicyclo[3.3.0]octane unit of dibromopalau'amine was prepared with complete diastereoselectivity in the polycyclic core from a tricyclic precursor. The key transformations of this sequence include (a) a Pummerer reaction-mediated oxidative bicyclization, and (b) a Wolff rearrangement-based ring contraction to deliver the strained azabicyclo[3.3.0]octane core.
Feldman
Ken S
KS
Chemistry Department, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu
Nuriye
Ahmed Yimam
AY
D017605:Bromine Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D006146:Guanidines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D017605:Bromine Compounds; D006146:Guanidines; D013141:Spiro Compounds; C438976:palau'amine