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Excising an olefin Plants produce an abundance of structurally complex terpene compounds that are useful precursors to pharmaceuticals and other fine chemicals. However, the carbon frameworks of these compounds constrain the available pathways for diversification. Smaligoet al. now show that successive treatment with ozone, an iron oxidant, and a hydrogen-atom donor can cleanly cleave pendant olefins from terpenes and related compounds (see the Perspective by Caille). Breaking the bond between saturated and double-bonded carbon centers offers a direct route to desirable chiral intermediates from readily available, inexpensive precursors.Science , this issue p.681 ; see also p.635

Hydrodealkenylative C(sp 3 )–C(sp 2 ) bond fragmentation

Hydrodealkenylative C(sp ³ )–C(sp ² ) bond fragmentation