R. Bell, M. Gravestock
Oct 1, 1969
Citations
0
Influential Citations
6
Citations
Journal
Canadian Journal of Chemistry
Abstract
The configuration and stereochemistry of methyl 11α-bromo-12-oxopodocarpan-19-oate 1 have been determined by application of the nuclear Overhauser effect. The dehydrobromination of 1 with dimethylacetamide–calcium carbonate results in a predominant 1,4-elimination process which for short reaction periods yields the non-conjugated ketone 8 and for long reaction periods yields the conjugated ketone 2. The 1,2-elimination of hydrogen bromide is a minor process and takes place to the extent of 20–22%. The ketone 8 has been oxidatively cleaved to the keto-acid 11, a valuable intermediate for the synthesis of bicyclic diterpenoids.