Inner-outer ring 1,3-bis(trimethylsilyloxy)-1,3-dienes as useful intermediates in the synthesis of helicenes.

Real, M. M.; Pérez Sestelo, J.; Sarandeses, L. A.


Tetrahedron Lett. 2002, 43, 9111–9114 (DOI: 10.1016/S0040-4039(02)02246-3).

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Functionalized benzo[c]phenanthrenes ([4]helicenes) and [5]helicenes were synthesised in five steps from tetrahydronaphthalenone and tetrahydrophenanthrenone compounds using a novel synthetic approach based on a Diels–Alder reaction between inner–outer ring 1,3-bis(trimethylsilyloxy)-1,3-dienes and benzyne or quinones.