Regioselective suprafacial 1,5-hydrogen shifts in o-quinodimethanes; a route to 4-deoxypodophyllotoxin
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 16,p. 1095-1096
- https://doi.org/10.1039/c39880001095
Abstract
The o-quinodimethane intermediate (4a) with cis-CO2Me groups undergoes regioselective 1,5-hydrogen shift to the cis-dihydronaphthalene (5a) whilst its trans-isomer (9a) gives both 1,5-hydrogen shift products (6a) and (7a); (5a) is readily converted into 4-deoxypodophyllotoxin.Keywords
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