Enantio- and Diastereoselective Synthesis of Latanoprost using an Organocatalyst

被引：19

作者：

Kawauchi, Genki ^{[1
]}

Umemiya, Shigenobu ^{[1
]}

Taniguchi, Tohru ^{[2
]}

Monde, Kenji ^{[2
]}

Hayashi, Yujiro ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan

[2] Hokkaido Univ, Fac Adv Life Sci, Frontier Res Ctr Adv Mat & Life Sci, Kita 21 Nishi 11, Sapporo, Hokkaido 0010021, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 33期

基金：

日本学术振兴会;

关键词：

asymmetric synthesis; cycloaddition; epimerization; organocatalysis; total synthesis; ASYMMETRIC ALPHA-AMINOXYLATION; VIBRATIONAL CIRCULAR-DICHROISM; CONVERSION NEF REACTION; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; MECHANISTIC INSIGHTS; ALDEHYDES; KETONES; BIMATOPROST; REDUCTION;

D O I：

10.1002/chem.201800829

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioselective total synthesis of latanoprost was achieved. Its chiral cyclopentane core structure was constructed through an organocatalyst-mediated [3+2]-cycloaddition reaction, and chirality in the -side chain was generated by prolinate-anion-mediated -aminoxylation of an aldehyde. Highly diastereoselective domino acetalization and an oxy-Michael reaction were key steps for the generation of C9 chirality.

引用

页码：8409 / 8414

页数：6

共 50 条

[41] Diisopinocampheylborane-Mediated Reductive Aldol Reactions: Highly Enantio- and Diastereoselective Synthesis of syn Aldols from N-Acryloylmorpholine [J].

Nuhant, Philippe ;

Allais, Christophe ;

Roush, William R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (33) :8703-8707

[42] Thiourea-Catalyzed Highly Enantio- and Diastereoselective Additions of Oxindoles to Nitroolefins: Application to the Formal Synthesis of (+)-Physostigmine [J].

Bui, Tommy ;

Syed, Salahuddin ;

Barbas, Carlos F., III .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) :8758-+

[43] Enantio- and Diastereoselective Synthesis of exo-Peroxyacetals: An Organocatalyzed Peroxyhemiacetalization/oxa-Michael Addition Cascade [J].

Maity, Sanjay ;

Parhi, Biswajit ;

Ghorai, Prasanta .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (27) :7723-7727

[44] Novel Diarylprolinol-derived Amino Perfluoroalkanesulfonamide Catalysts: Highly Enantio- and Diastereoselective Aldol Reaction [J].

Lutete, Leopold M. ;

Ikemoto, Tetsuya .

CHEMISTRY LETTERS, 2017, 46 (04) :577-579

[45] A Sequential O-Nitrosoaldol and Grignard Addition Process: An Enantio- and Diastereoselective Entry to Chiral 1,2-Diols [J].

Jiao, Peng ;

Kawasaki, Masanori ;

Yamamoto, Hisashi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (18) :3333-3336

[46] Enantio- and Diastereoselective Assembly of Tetrahydrofuran and Tetrahydropyran Skeletons with All-Carbon-Substituted Quaternary Stereocenters [J].

Chen, Zhilong ;

Sun, Jianwei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (51) :13593-13596

[47] Enantio- and Diastereoselective Copper-Catalyzed Synthesis of Chiral Aziridines with Vicinal Tetrasubstituted Stereocenters [J].

Xie, Fang ;

Zhao, Jie ;

Ren, Deyue ;

Xue, Jianming ;

Wang, Jingyi ;

Zhao, Qin ;

Liu, Lu ;

Liu, Xiaodan .

ORGANIC LETTERS, 2023, 25 (47) :8530-8534

[48] Enantio- and diastereoselective boron conjugate addition to α-alkyl α,β-unsaturated esters [J].

Li, Meng ;

Peng, Guang-Rui ;

Yang, Xuan ;

Ma, Zhen-Ning ;

Xie, Jian-Bo .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 21 (01) :53-58

[49] Direct Catalytic Enantio- and Diastereoselective Mannich Reaction of Isocyanoacetates and Ketimines [J].

Ortin, Irene ;

Dixon, Darren J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (13) :3462-3465

[50] Merging chiral organocatalysts: enantio- and diastereoselective direct vinylogous Mannich reaction of alkylimines [J].

Xiong, Xiao-Feng ;

Jia, Zhi-Jun ;

Du, Wei ;

Jiang, Kun ;

Liu, Tian-Yu ;

Chen, Ying-Chun .

CHEMICAL COMMUNICATIONS, 2009, (45) :6994-6996

← 1 2 3 4 5 →