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

[1] Enantio- and diastereoselective synthesis of erysulfone and erysulfoxide
Bourdeau, L
Sutherland, AG
TETRAHEDRON LETTERS, 1997, 38 (52) : 9081 - 9084
[2] Enantio- and diastereoselective synthesis of γ-amino alcohols
Verkade, Jorge M. M.
Quaedflieg, Peter J. L. M.
Verzijl, Gerard K. M.
Lefort, Laurent
van Delft, Floris L.
de Vries, Johannes G.
Rutjes, Floris P. J. T.
CHEMICAL COMMUNICATIONS, 2015, 51 (77) : 14462 - 14464
[3] Enantio- and diastereoselective synthesis of (R,R)-β-Methoxytyrosine
Cranfill, David C.
Lipton, Mark A.
ORGANIC LETTERS, 2007, 9 (18) : 3511 - 3513
[4] Enantio- and Diastereoselective Synthesis of Spiro-epoxyoxindoles
Boucherif, Amina
Yang, Qing-Qing
Wang, Qiang
Chen, Jia-Rong
Lu, Liang-Qiu
Xiao, Wen-Jing
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09): : 3924 - 3929
[5] Enantio- and Diastereoselective Synthesis of β,γ,γ,δ-Tetrasubstituted α-Methylene-δ-lactones
Albrecht, Lukasz
Deredas, Dariusz
Wojciechowski, Jakub
Wolf, Wojciech M.
Krawczyk, Henryk
SYNTHESIS-STUTTGART, 2012, 44 (02): : 247 - 252
[6] Enantio- and diastereoselective synthesis of 4′-α-substituted carbocyclic nucleosides
Kato, K
Suzuki, H
Tanaka, H
Miyasaka, T
TETRAHEDRON-ASYMMETRY, 1998, 9 (06) : 911 - 914
[7] Enantio- and diastereoselective Darzens condensations
Achard, Thierry J. R.
Belokon', Yuri N.
Ilyin, Michael
Moskalenko, Margarita
North, Michael
Pizzato, Francesca
TETRAHEDRON LETTERS, 2007, 48 (17) : 2965 - 2969
[8] Enantio- and diastereoselective synthesis of all four stereoisomers of formoterol
Hett, R
Fang, QK
Gao, Y
Hong, YP
Butler, HT
Nie, XY
Wald, SA
TETRAHEDRON LETTERS, 1997, 38 (07) : 1125 - 1128
[9] Tandem catalytic enantio- and diastereoselective synthesis of cyclopropyl alcohols using aryl aldehydes
Kim, Hun Young
Walsh, Patrick J.
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2012, 25 (11) : 933 - 938
[10] Enantio- and diastereoselective Michael addition reactions of α-cyanoketones to nitroalkenes catalyzed by binaphthyl-derived organocatalyst
Lee, Hyun Joo
Woo, Saet Byeol
Kim, Dae Young
TETRAHEDRON LETTERS, 2012, 53 (26) : 3374 - 3377

← 1 2 3 4 5 →