Metamorphosis of cycloalkenes for the divergent total synthesis of polycyclic indole alkaloids

被引：142
作者：
Xu, Zhengren [1 ,2 ]
Wang, Qian [1 ]
Zhu, Jieping [1 ]
机构：
[1] Ecole Polytech Fed Lausanne, Lab Synth & Nat Prod, Inst Chem Sci & Engn, SB,ISIC,LSPN, BCH5304, CH-1015 Lausanne, Switzerland
[2] Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
来源：
CHEMICAL SOCIETY REVIEWS | 2018年 / 47卷 / 21期
基金：
瑞士国家科学基金会;
关键词：
ENANTIOSELECTIVE TOTAL SYNTHESES; MERSICARPINE ALKALOIDS; (+)-LEUCONODINE F; NATURAL-PRODUCTS; LEUCONOXINE; (+/-)-ASPIDOSPERMIDINE; (+/-)-GONIOMITINE; LEUCONODINES; INTERMEDIATE;
D O I：
10.1039/c8cs00454d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
From tryptamine and secologanine, nature generates monoterpene indole alkaloids with an unprecedented level of skeletal diversity through a couple-divert' sequence. Intrigued by this biosynthetic machinery, new strategies and tactics to access skeletally distinct natural products are continuously emerging. In this Tutorial Review, we'll present a simplified view of nature's logic for biosynthesis and the representative strategies and tactics developed for the divergent total synthesis of monoterpene indole alkaloids. Our group has been developing a couple-divert' approach with the strategic use of cycloalkene as a pluripotent motif in the synthetic design and has developed an integrated oxidation/reduction/cyclization (iORC) sequence for transforming functionalized cycloalkenes, easily available by a variety of cross-coupling reactions, to skeletally diverse natural products. The integration of controlled regio-, chemo- and stereo-selective cyclization and heteroannulation reactions into these domino sequences will be highlighted.
引用
收藏
页码：7882 / 7898
页数：17
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