Alkynyliodonium salts in organic synthesis. Application to the total synthesis of the tropoloisoquinoline alkaloid pareitropone.
The synthesis of the tropoloisoquinoline alkaloid pareitropone has been accomplished in 14 steps from 2,3,4-trimethoxybenzoic acid. The key transformations include the generation of an alkylidenecarbene intermediate through intramolecular addition of a tosylamide anion to an alkynyliodonium salt, and the cycloaddition of that carbene to a peri positioned aromatic ring to afford a cycloheptatrienylidene product featuring the intact pareitropone skeleton.
Feldman
Ken S
KS
Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA. ksf@chem.psu.edu
Cutarelli
Timothy D
TD
D000470:Alkaloids / Q000138:chemical synthesis*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis; D006838:Hydrocarbons; D007546:Isoquinolines / Q000138:chemical synthesis*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D009861:Onium Compounds / Q000737:chemistry*
D000470:Alkaloids; D000972:Antineoplastic Agents, Phytogenic; D006838:Hydrocarbons; D007546:Isoquinolines; D009861:Onium Compounds; C467752:pareitropone; C030011:carbene; D008697:Methane