The highly oxygenated diterpene ingenol represents a formidable synthetic challenge. Our planned approach to the ingenol A ring utilises a stereospecific and chemoselective 1,5 alkylidene carbene C-H insertion reaction.The feasibility of this reaction has been tested on model compounds 1 , derived from stereoselective manipulation of appropriately substituted 8-oxabicyclo[3.2.1]octan-3-one ring systems. The ratio of cyclopentenes 2  to 3  depends on the O-substituents P and P' and C-substituents R and R'.

Selective alkylidene carbene insertion reactions: Studies towards the synthesis of ingenol

244th National Meeting (2012)

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