Practical synthesis and Diels-Alder chemistry of [4]dendralene

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Payne, Alan
Willis, Anthony
Sherburn, Michael

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American Chemical Society

Abstract

Spectacular new atom efficient domino cycloaddition sequences involving [4]dendralene, the simplest cross-conjugated tetraene, are reported. Up to eight stereocenters, three new rings, and six C-C bonds are generated in one synthetic operation. The site selectivity of dienophile addition to cross-conjugated trienes and tetraenes is controlled with a simple Lewis acid.

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Journal of the American Chemical Society

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2037-12-31