Organic Chemistry

A Stereoselective Photoinduced Cycloisomerization Inspired by Ophiobolin A



A concise, modular, and stereoselective synthetic entry point to the 5-8-5 carbocyclic core of the ophiobolins is described. This strategy exploits the chiral tertiary alcohol of ophiobolin A to guide assmebly of the 5-8-5 scaffold in a single step via photoinitiated isomerization. Mechanistic insights into the origin of stereocontrol in this reaction are described, as are efforts to elaborate the resultant 5-8-5 polycycle to the pharmacophore of ophiobolin A.


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Supplementary material

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Supporting Information
Detailed procedures, characterization data for organic compounds, and computational data.