Enantio- and Diastereoselective Synthesis of Latanoprost using an Organocatalyst

被引：18

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

[31] Highly enantio- and diastereoselective synthesis of α-trifluoromethyldihydropyrans using a novel bifunctional piperazine-thiourea catalyst
Li, Peng
Chai, Zhuo
Zhao, Sheng-Li
Yang, Ying-Quan
Wang, Hai-Feng
Zheng, Chang-Wu
Cai, Yue-Peng
Zhao, Gang
Zhu, Shi-Zheng
CHEMICAL COMMUNICATIONS, 2009, (47) : 7369 - 7371
[32] Enantio- and Diastereoselective Iodocyclopropanation of Allylic Alcohols by Using a Substituted Zinc Carbenoid
Beaulieu, Louis-Philippe B.
Zimmer, Lucie E.
Charette, Andre B.
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (44) : 11829 - 11832
[33] Highly Enantio- and Diastereoselective Synthesis of β-Methyl-γ-monofluoromethyl-Substituted Alcohols
Yang, Wenguo
Wei, Xinle
Pan, Yuanhang
Lee, Richmond
Zhu, Bo
Liu, Hongjun
Yan, Lin
Huang, Kuo-Wei
Jiang, Zhiyong
Tan, Choon-Hong
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (29) : 8066 - 8070
[34] Synthesis of Atropisomeric Hydrazides by One-Pot Sequential Enantio- and Diastereoselective Catalysis
Portolani, Chiara
Centonze, Giovanni
Luciani, Sara
Pellegrini, Andrea
Righi, Paolo
Mazzanti, Andrea
Ciogli, Alessia
Sorato, Andrea
Bencivenni, Giorgio
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (42)
[35] Enantio- and diastereoselective synthesis of anti-α-bromo-α-fluoro-β-hydroxycarboxylates
Iseki, K
Kuroki, Y
Kobayashi, Y
SYNLETT, 1998, (04) : 437 - +
[36] Enantio- and diastereoselective construction of α,α-disubstituted α-amino acids for the synthesis of biologically active compounds
Ohfune, Y
Shinada, T
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (24) : 5127 - 5143
[37] Enantio- and Diastereoselective Total Synthesis of Belzutifan Enabled by Rh-Catalyzed Hydrogenation
Le, Diane N.
Johnson, Heather C.
Lam, Yu-hong
Sun, Chunrui
Cheng, Lili
Belyk, Kevin M.
ORGANIC LETTERS, 2024, 26 (19) : 4059 - 4064
[38] Highly Enantio- and Diastereoselective One-Pot Methods for the Synthesis of Halocyclopropyl Alcohols
Kim, Hun Young
Salvi, Luca
Carroll, Patrick J.
Walsh, Patrick J.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (03) : 954 - 962
[39] Enantio- and Diastereoselective Synthesis of syn-β-Hydroxyallylsilanes via a Chiral (Z)-γ-Silylailylboronate
Lira, Ricardo
Roush, William R.
ORGANIC LETTERS, 2007, 9 (21) : 4315 - 4318
[40] Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles
Chintalapudi, V.
Galvin, E. A.
Greenaway, R. L.
Anderson, E. A.
CHEMICAL COMMUNICATIONS, 2016, 52 (04) : 693 - 696

← 1 2 3 4 5 →