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

被引：22
作者：
Han, Jing-Chun [1 ]
Liu, Lian-Zhu [1 ]
Chang, Yuan-Yuan [1 ]
Yue, Guo-Zong [1 ]
Guo, Jie [1 ]
Zhou, Li-Yan [1 ]
Li, Chuang-Chuang [1 ]
Yang, Zhen [1 ,2 ,3 ]
机构：
[1] Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China
[2] Peking Univ, Coll Chem, Peking Tsinghua Ctr Life Sci, Minist Educ,Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
[3] Peking Univ, Coll Chem, Peking Tsinghua Ctr Life Sci, BNLMS, Beijing 100871, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 11期
基金：
美国国家科学基金会;
关键词：
5-7-6 TRICYCLIC CORE; STEREOSELECTIVE-SYNTHESIS; DITERPENE; GUANACASTEPENE; CONSTRUCTION; HYDROXYLATION; DIMERIZATION; OXIDATION; ALKALOIDS; PROGRESS;
D O I：
10.1021/jo4006156
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 sp(2) carbon at C(2) in substrate 8 is a critical factor for the formation of the tricyclic [5-7-6] skeleton in 7.
引用
收藏
页码：5492 / 5504
页数：13
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