Synthetic Studies on the Ingenane Diterpenes. An Improved Entry into a trans-Intrabridgehead System

Autor: Rigby, J. H., Bazin, B., Meyer, J. H., Mohammadi, F.
Zdroj: Organic Letters; March 2002, Vol. 4 Issue: 5 p799-801, 3p
Abstrakt: The efficient construction of an ingenol intermediate exhibiting “inside−outside” intrabridgehead stereochemistry is reported. The sequence features the net conversion of a cis-intrabridgehead compound into a highly strained trans-species via palladium-mediated isomerization of an allylic epoxide followed by a low-temperature alkoxide-accelerated 1,5-hydrogen migration.
Databáze: Supplemental Index