jo4006156_si_002.cif (47.68 kB)
Asymmetric Total Synthesis of Caribenol A via an Intramolecular Diels–Alder Reaction
dataset
posted on 2013-06-07, 00:00 authored by Jing-Chun Han, Lian-Zhu Liu, Yuan-Yuan Chang, Guo-Zong Yue, Jie Guo, Li-Yan Zhou, Chuang-Chuang Li, Zhen YangA 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.