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Synthetic Study of 1,3-Butadiene-Based IMDA Approach to Construct a [5−7−6] Tricyclic Core and Its Application to the Total Synthesis of C8-epi-Guanacastepene O

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journal contribution
posted on 01.09.2006, 00:00 by Chuang-Chuang Li, Cui-Hua Wang, Bo Liang, Xin-Hao Zhang, Lu-Jiang Deng, Shuang Liang, Jia-Hua Chen, Yun-Dong Wu, Zhen Yang
An efficient intramolecular Diels−Alder (IMDA) strategy for the construction of the [5−7−6] tricyclic core (18) of guanacastepenes has been developed from cis- and trans-1,3-butadiene-tethered 4-oxopent-2-ynoic acid ethyl esters 10 and 11. This method facilitates the synthesis of C8-epi-guanacastepene O (36) in a very efficient manner.