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Asymmetric Total Synthesis of Caribenol A via an Intramolecular Diels–Alder Reaction

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posted on 07.06.2013, 00:00 by Jing-Chun Han, Lian-Zhu Liu, Yuan-Yuan Chang, Guo-Zong Yue, Jie Guo, Li-Yan Zhou, Chuang-Chuang Li, Zhen Yang
A total synthesis of the caribenol A (1), a novel natural product with an intriguing tetracyclic framework, has been achieved. The synthesis features an intramolecular Diels–Alder (IMDA) reaction for the facile construction of the tricyclic [5–7–6] skeleton of caribenol A (1) and a biomimetic oxidation reaction for the formation of the 2-hydroxyfuran-2­(5H)-one motif of caribenol A (1) as key steps. This synthetic approach also reveals that the sp2 carbon at C(2) in substrate 8 is a critical factor for the formation of the tricyclic [5–7–6] skeleton in 7.