Total Synthesis of Sinensilactam A

被引：31
|
作者：
Shao, Wenbin [1 ]
Huang, Jun [1 ]
Guo, Kai [1 ]
Gong, Jianxian [1 ]
Yang, Zhen [1 ,2 ,3 ,4 ]
机构：
[1] Peking Univ, Shenzhen Grad Sch, Key Lab Chem Genom, State Key Lab Chem Oncogen, Shenzhen 518055, Peoples R China
[2] Peking Univ, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
[3] Peking Univ, Coll Chem & Mol Engn, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China
[4] Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 07期
基金：
美国国家科学基金会;
关键词：
N-ACYLIMINIUM IONS; INTERMOLECULAR ADDITION-REACTIONS; FORMAL TOTAL-SYNTHESIS; POLYCYCLIC MEROTERPENOIDS; BIOSYNTHETIC-PATHWAY; DIVERGENT SYNTHESIS; A-G; DISCOVERY; ACID; METABOLITES;
D O I：
10.1021/acs.orglett.8b00380
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of naturally occurring (+/-)-sinensilactam A was achieved in 18 steps. The key steps of this work are a rhodium-catalyzed [3 + 2] cydoaddition for construction of the two all-carbon vicinal quaternary centers and a convergent and tandem condensation of the in situ generated N-acyliminium intermediate with aldehyde 20. This enabled implementation of a unified strategy for stereoselective formation; of the tetracyclic hemiaminal core of sinensilactam A in a later stage. The total syntheses of applanatumol F and C8-epi-applanatumol D are also achieved using this strategy.
引用
收藏
页码：1857 / 1860
页数：4
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