The formal homo-Nazarov reaction (ring-opening cyclization of alkenyl cyclopropyl ketones) is recognized as a practical and versatile method for the construction of carbocyclic and heterocyclic scaffolds seen in a broad range of biologically active natural and synthetic compounds. Herein, we disclose the first example of an intramolecular interrupted formal homo-Nazarov cyclization involving alkenyl cyclopropyl ketones with tethered (hetero)arenes. Using catalytic SnCl<sub>4</sub>, these alkenyl cyclopropyl ketones undergo ring-opening cyclization to form six-membered cyclic oxyallyl cations which are immediately trapped by the tethered (hetero)arenes in a Friedel-Crafts-type arylation to access fused polycyclic scaffolds, such as the naturally-occurring abietane skeleton. This highly amendable oxyallyl intramolecular trapping protocol provides facile access to natural product-based and medicinally-relevant polycyclic cores in a single step transformation while utilizing mild reaction conditions.

Intramolecular interrupted formal homo-Nazarov cyclization using tethered (hetero)arenes: Facile access to fused carbocycles and heterocycles

ACS Fall 2021

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