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

页码：5492 / 5504

页数：13

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