Enantioselective approach to the hetisine alkaloids. Synthesis of the 3-methyl-1-aza-tricyclo[5.2.1.0(3,8)]decane core via intramolecular dipolar cycloaddition.
[structure: see text]. An efficient, enantioselective approach to the hetisine class of the C(20)-diterpenoid alkaloids is described. The strategy involves an intramolecular oxidopyridinium dipolar cycloaddition as the key transformation, in which simultaneous formation of the C5-C6 and C10-C20 bonds in the 3-methyl-1-aza-tricyclo[5.2.1.0(3,8)]decane core of the hetisine alkaloids is effected.
Peese
Kevin M
KM
Department of Chemistry, University of Illinois, Urbana, 61801, USA.
Gin
David Y
DY
D031841:Aconitum / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000145:classification; D000473:Alkanes; D001952:Bridged-Ring Compounds / Q000737:chemistry; D031882:Delphinium / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000145:classification; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry; D029626:Ranunculaceae / Q000737:chemistry
D000470:Alkaloids; D000473:Alkanes; D001952:Bridged-Ring Compounds; D004224:Diterpenes; D011083:Polycyclic Compounds; C111428:kobusine; C012867:decane