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In …︁ out …︁ shake it all about! The tetracyclic core of ingenol has been prepared in a convergent synthesis. The pinacol‐type rearrangement of an epoxy alcohol provides a simple, expedient solution to the challenging “inside–outside” intrabridgehead stereochemistry of ingenol (see scheme, TBS=tert‐butyldimethylsilyl).

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A simple one-pot procedure for the Sakurai-Prins-Ritter sequence allows rapid assembly of 4-acylamino-2,6-substituted tetrahydropyrans in high yields and with excellent diastereoselectivity from readily available 4-acetoxy-1,3-dioxanes, allylsilanes, and nitriles. A variety of nitriles have been shown to participate. Diastereoselectivities are uniformly high and observed stereochemistry of cation trapping proceeds according to Alder's model of the 4-tetrahydropyranyl cation.