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5-7 Ring Systems
Cacospongionolide B
15F2 Isoprostanes
Enantioselective Silylation
Tandem Metathesis Reactions
Diversity Oriented Synthesis


Total Synthesis of Cycloaranosene

Researcher - Stephanie Ng

Stephanie Ng


Both inter- and intramolecular [2+2] photocycloadditions of functionalized cyclobutenes have been explored in the Snapper laboratories. Thermolysis of the resulting strained cycloadducts allow for rapid entry into 5-8-5 ring systems commonly found in a variety of natural products. We are able to apply an intramolecular photocycloaddition followed by a thermolysis toward completing the total synthesis of Cycloaraneosene.


“Intramolecular [2+2]-Photocycloaddition/Thermal Fragmentation Approach toward 5-8-5 Ring Systems” Priscilla C.-K. Lo, Marc L. Snapper Org. Lett. 2001, 3, 2819-2821.
“[2+2]-Photocycloaddition/Thermal Retrocycloaddition.  A New Entry into Functionalized 5-8-5 Ring Systems” Michele L. Randall, Priscilla C.-K. Lo, Peter J. Bonitatebus, Jr., Marc L. Snapper J. Am. Chem. Soc. 1999, 121, 4534-4535.

Merkert Chemistry Center, Rms 337 & 339
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