Chemistry of the Podocarpaceae. XXV. Conversion of 8α,13β-epoxylabd-14-en-2-one into compounds with ambergris-type odours

Abstract

2-Oxomanoyl oxide (2) has been converted into the 2-hydroxy ether (17) and the 2-keto ether (19), both of which possess ambergris-type odours similar to but much weaker than that of the odoriferous compound (14). The route affording the highest overall yield is via the intermediates (5), (43), (23), and (39), which gives 23% of the 2-keto ether (19) and 17% of the hydroxy ether (17).