CHEM 215HH W13 SSG 5.9 - Lawrence Chen, Kelly Compton, & Kelsey McKinney

Synthesis of Tubingensin A: Triene 12 to Hexacyclic Lactol 27
Bian, M.; Wang, Z.; Xiong, X.; Sun, Y.; Matera, C.; Nicolaou, K. C.; Li, A. J. Am. Chem. Soc. 2012, 134, 8078-8081.

First isolated from the fungal genus Aspergillus, compounds such as Tubingensin A have been seen to express anti-insectant, antiviral, and anticancer activity. Intermediate 27 in particular is formed by a CuOTf-promoted 6-pi e- electrocyclization ring closure/ aromatization.

Tubingensin A

Reaction Scheme and Intermediates