Total synthesis of the tropoloisoquinoline alkaloid pareitropone via alkynyliodonium salt chemistry and related studies.
The first chemical synthesis of pareitropone, by a route featuring application of alkynyliodonium salt chemistry, is described. The key transform initiates with addition of an alkylidenecarbene, derived by intramolecular nucleophile addition to the alkynyliodonium moiety, to a proximal aromatic ring. This addition delivers a highly strained norcaradiene substructure that rapidly reorganizes to furnish the pareitropone skeleton.
Feldman
Ken S
KS
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu
Cutarelli
Timothy D
TD
Di Florio
Romina
R
D000470:Alkaloids / Q000138:chemical synthesis*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D006838:Hydrocarbons; D007546:Isoquinolines / Q000138:chemical synthesis*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*
D000470:Alkaloids; D000972:Antineoplastic Agents, Phytogenic; D006838:Hydrocarbons; D007546:Isoquinolines; D009861:Onium Compounds; C467752:pareitropone; C030011:carbene; D008697:Methane