Nakafuran synthesis

Trimethylsilyl)diazomethane was also applied successfully to the total synthesis of pinguisane-type sesquiterpenes for the ring expansion (9-12) of the bicycloocte-none 9.16 by Uyehara et al. (1986). The same authors used (trimethylsilyl)diazome-thane for the ring expansion of the bicyclic ketone 9.17 (9-13) in studies on the synthesis of the novel sesquiterpenoid ( ) nakafuran-8, a bicyclo[4.2.2]decadiene with antifeedant properties (Uyehara et al., 1992). 

Tanis, S.P. and Herrinton, P.M. (1985) Furans in synthesis. 5. Furan-terminated cationic cydizations in the preparation of fused, spirocydic and bridged ring systems. An application to the synthesis of nakafuran 9. J. Org. Chem., 5, 3988-3996. 

Uyehara, T, Sugimoto, M., Suzuki, L, and Yamamoto, Y. (1989) Total synthesis of ( )-nakafuran-8, marine metabolite with antifeedant properties based on formal bridgehead substitution of a bicyclo[2 2 2J oct-5-en-2-one system. J. Chem. Soc. Chem. Commun., 1841-1842. 

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