The total synthesis of (+)-hapalindole Q by an organomediated Diels-Alder reaction.
The total synthesis of (+)-hapalindole Q has been achieved. The key step is a Diels-Alder reaction mediated by MacMillan's organocatalyst to provide the critical intermediate with high enantioselectivity (93% ee). This step establishes the proper arrangement of the required four contiguous stereocenters, including the quaternary center, and represents the first successful application of an enantioselective organomediated Diels-Alder reaction in total synthesis.
Kinsman
Aaron C
AC
Department of Chemistry, University of Western Ontario, London, Ontario, N6A 5B7, Canada.
Kerr
Michael A
MA
D000458:Cyanobacteria / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007211:Indoles; C438931:hapalindole Q