Synthesis of cyclic hemiketals and spiroketals from dioxanorbornanes.
[reaction: see text] A new method for the synthesis of substituted pyranone hemiketals from dioxanorbornanes via SmI(2) is described. Also reported is a synthesis of spiro[4.5]ketals from analogous intermediates via acid-promoted deprotection/ketalization.
Winkler
Jeffrey D
JD
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. winkler@sas.upenn.edu
Mikochik
Peter J
PJ
D001892:Camphanes / Q000737:chemistry*; D003500:Cyclization
D001892:Camphanes