Synthetic studies toward the kempane diterpenes. Construction of a key tricyclic intermediate
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A synthetic sequence is described for construction of the tricyclic portion (35) of kempane diterpenes. The central stereochemistry was established by a Diels-Alder addition of 2,6-dimethyl-para-benzoquinone to a 5-membered, dithiane-protected diene, and the addition of acetylide, with very high chemoselectivity, provided a suitably functionalized handle that will be incorporated into the final seven-membered ring. The remaining stereogenic centres about the decalin moiety were established by a series of equilibration and reduction steps.
Bao, GL, L. Zhao, and DJ Burnell. 2005. "Synthetic studies toward the kempane diterpenes. Construction of a key tricyclic intermediate." Organic & Biomolecular Chemistry 3(19): 3576-3584.