Alkynyliodonium salts in organic synthesis. Application to the total synthesis of the tropoloisoquinoline alkaloid pareitropone.

Ken S Feldman, Timothy D Cutarelli

Index: J. Am. Chem. Soc. 124(39) , 11600-1, (2002)

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Abstract

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.