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

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