Organocatalytic, Asymmetric Total Synthesis of (-)-Haliclonin A

被引：56

作者：

Guo, Lian-Dong ^{[1
,2
]}

Huang, Xiong-Zhi ^{[1
,2
]}

Luo, Shi-Peng ^{[1
,2
]}

Cao, Wen-Sen ^{[1
,2
]}

Ruan, Yuan-Ping ^{[1
,2
]}

Ye, Jian-Liang ^{[1
,2
]}

Huang, Pei-Qiang ^{[1
,2
,3
]}

机构：

[1] Xiamen Univ, Coll Chem & Chem Engn, iChEM Collaborat Innovat Ctr Chem Energy Mat, Dept Chem, Xiamen 361005, Fujian, Peoples R China

[2] Xiamen Univ, Coll Chem & Chem Engn, iChEM Collaborat Innovat Ctr Chem Energy Mat, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Fujian, Peoples R China

[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 12期

基金：

中国国家自然科学基金;

关键词：

alkaloids; macrocycles; metathesis; natural products; total synthesis; ENANTIOSELECTIVE TOTAL-SYNTHESIS; CARBON QUATERNARY STEREOCENTERS; CLOSING ALKYNE METATHESIS; SPONGE RENIERA-SARAI; SILYL ENOL ETHERS; CONJUGATE ADDITION; ALPHA; BETA-UNSATURATED KETONES; ORGANIC-SYNTHESIS; MICHAEL ADDITION; ALDOL REACTIONS;

D O I：

10.1002/anie.201512005

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of the alkaloid (-)-halicloninA is reported. The asymmetric synthesis relied on a novel organocatalytic asymmetric conjugate addition of nitromethane with 3-alkenyl cyclohex-2-enone to set the stereochemistry of the all-carbon quaternary stereogenic center. The synthesis also features a Pd-promoted cyclization to form the 3-azabicyclo[3,3,1]nonane core, a SmI2-mediated intermolecular reductive coupling of enone with aldehyde to form the requisite secondary chiral alcohol, ring-closing alkene and alkyne metathesis reactions to build the two aza-macrocyclic ring systems, and an unprecedented direct transformation of enol into enone.

引用

页码：4064 / 4068

页数：5

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