Total synthesis of (+/-)-hapalindole Q.
[reaction: see text] The total synthesis of the antibacterial and antimycotic alkaloid hapalindole Q has been achieved in eight steps and 12.4% overall yield. The key step involves a regio- and diastereoselective Diels-Alder reaction to afford a bicyclo[2.2.2]oct-2-ene. This cycloadduct was subsequently dihydroxylated, cleaved, and converted to the natural product.
Kinsman
A C
AC
Department of Chemistry, University of Western Ontario, London, Ontario N6A 5B7, Canada.
Kerr
M A
MA
D000470:Alkaloids / Q000138:chemical synthesis*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000458:Cyanobacteria / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*
D000470:Alkaloids; D000900:Anti-Bacterial Agents; D007211:Indoles; C438931:hapalindole Q