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

Li, Chuang-Chuang; Wang, Cui-Hua; Liang, Bo; Zhang, Xin-Hao; Deng, Lu-Jiang; Liang, Shuang; Chen, Jia-Hua; Wu, Yun-Dong; Yang, Zhen

doi:10.1021/jo060996h.s003

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

journal contribution

posted on 2006-09-01, 00:00 authored 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.