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

共 50 条

[1] Total Synthesis of Haliclonin A
Jin, Yuan
Orihara, Kensuke
Kawagishi, Fumiki
Toma, Tatsuya
Fukuyama, Tohru
Yokoshima, Satoshi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (17) : 9666 - 9671
[2] Catalytic Asymmetric Total Synthesis of Macrocyclic Marine Natural Product (-)-Haliclonin A
Luo, Shi-Peng
Huang, Xiong-Zhi
Guo, Lian-Dong
Huang, Pei-Qiang
CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (12) : 1723 - 1736
[3] Enantioselective total synthesis of the alkaloid (-)-haliclonin A
Huang, Peiqiang
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
[4] Asymmetric organocatalytic methods for the synthesis of tetrahydropyrans and their application in total synthesis
Vetica, Fabrizio
Chauhan, Pankaj
Dochain, Simon
Enders, Dieter
CHEMICAL SOCIETY REVIEWS, 2017, 46 (06) : 1661 - 1674
[5] Recent Applications of Asymmetric Organocatalytic Methods in Total Synthesis
Parella, Ramarao
Jakkampudi, Satish
Zhao, John C. -G.
CHEMISTRYSELECT, 2021, 6 (09): : 2252 - 2280
[6] An efficient organocatalytic route for asymmetric total synthesis of Stagonolide F
Shelke, Anil M.
Suryavanshi, Gurunath
TETRAHEDRON LETTERS, 2015, 56 (45) : 6207 - 6209
[7] Enantioselective Total Synthesis of (+)-Scuteflorin A Using Organocatalytic Asymmetric Epoxidation
Bartlett, Christopher J.
Day, David P.
Chan, Yohan
Allin, Steven M.
McKenzie, Michael J.
Slawin, Alexandra M. Z.
Page, Philip C. Bulman
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01): : 772 - 774
[8] Toward the Total Synthesis of Haliclonin A: Construction of a Tricyclic Substructure
Luo, Shi-Peng
Guo, Lian-Dong
Gao, Long-Hui
Li, Shuang
Huang, Pei-Qiang
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (01) : 87 - 91
[9] Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step
Enders, Dieter
Fronert, Jeanne
Bisschops, Tom
Boeck, Florian
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1112 - 1117
[10] Organocatalytic asymmetric synthesis of aziridines
Bew, Sean P.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236

← 1 2 3 4 5 →