The cyclobutane structural motif is common to a wide range of biologically active natural products. Some cyclobutane-containing natural products exhibit potent anti-inflammatory properties when subjected to various bioassays. Current treatments for inflammatory conditions such as rheumatoid arthritis and dermatitis show low receptor binding selectivity and, when administered, cause significant side affects. For this reason, it is beneficial to devise a synthetic method for bioactive cyclobutane and analogs to for medicinal applications.Although there are numerous methods for the intramolecular synthesis of cyclobutanes, methods to form the product intermolecularly and stereoselectively are still limited. A method for the direct synthesis of cyclobutanes employing a visible light-activated organic single electron oxidant will be presented. By implementation of this methodology, we have been able to synthesize a number of cyclobutane-containing natural products via radical cation intermediates by employing organic photocatalysts in mildly oxidizing reaction conditions. The scope, limitations, and mechanism of this synthetic methodology will be discussed.

Synthesis of naturally occuring cyclobutane compounds via photoinduced electron transfer

245th National Meeting (2013)

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