Synthesis of Prostaglandin Analogues, Latanoprost and Bimatoprost, Using Organocatalysis via a Key Bicyclic Enal Intermediate

被引：46

作者：

Prevost, Sebastien ^{[1
]}

Thai, Karen ^{[1
]}

Schuetzenmeister, Nina ^{[1
]}

Coulthard, Graeme ^{[1
]}

Erb, William ^{[1
]}

Aggarwal, Varinder K. ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 03期

基金：

英国工程与自然科学研究理事会; 欧洲研究理事会;

关键词：

ENANTIOSELECTIVE ALKYNYLATION; ASYMMETRIC-SYNTHESIS; CARBONYL ALLYLATION; ALLYLIC ALKYLATION; ALCOHOL OXIDATION; ALDEHYDES; REARRANGEMENT; PGF(2-ALPHA); REAGENTS; ESTERS;

D O I：

10.1021/ol503520f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF(2 pi), have been synthesized in just 7 and 8 steps, respectively. The syntheses employ an organocatalytic aldol reaction that converts succinaldehyde into a key bicyclic enal intermediate, which is primed for attachment of the required lower and upper side chains. By utilizing the crystalline lactone, the drug molecules were prepared in >99% ee.

引用

页码：504 / 507

页数：4

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