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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| Authors: | Li Chuang-Chuang Wang Cui-Hua Liang Bo Zhang Xin-Hao Deng Lu-Jiang Liang Shuang Chen Jia-Hua Wu Yun-Dong Yang Zhen |
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| Affiliation: | Key Laboratory of Bioorganic Chemistry and Molecular Engineering , Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Shenzhen Graduate School, Peking University, Beijing 100871, China. |
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| Abstract: | 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. |
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