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Synfacts 2011(12): 1311-1311  
DOI: 10.1055/s-0031-1289427
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Route to Functionalized Sumanenes

Contributor(s): Timothy M. Swager, John B. Goods
T. Amaya, M. Hifumi, M. Okada, Y. Shimizu, T. Moriuchi, K. Segawa, Y. Ando, T. Hirao*
Osaka University, Suita and Osaka University, Ibaraki, Japan
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Publication History

Publication Date:
18 November 2011 (online)

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Significance

The authors screened several types of oxidation conditions and ultimately produced trioxosumanene 3 in 73% yield. Though mono­oxosumanene 1 could be synthesized, the dioxo derivative was not produced in significant amount in any of the numerous conditions attempted. The authors demonstrated the potential for further functionalization by addition of a methyl Grignard to 3. This addition occurred in syn fashion to all three carbonyls via approach of the convex face.