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

共 48 条

[1] Aggarwal V. K., 2013, PCT Int. Appl., Patent No. [WO 2013/186550 A1, 2013186550]
[2] Bindra J. S., 1977, PROSTAGLANDIN SYNTHE
[3] Bovall D., 2000, ORG LETT, V2, P4233
[4] Tandem enyne metathesis and Claisen rearrangement: A versatile approach to conjugated dienes of variable substitution patterns
Clark, Daniel A.
Kulkarni, Amol A.
Kalbarczyk, Kyle
Schertzer, Bryan
Diver, Steven T.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (49) : 15632 - 15636
[5] Clissold D. W., 2005, Prostaglandin synthesis, Patent No. [2005058812A2, 2005058812, W02005058812A2]
[6] SYNTHESIS OF THERAPEUTICALLY USEFUL PROSTAGLANDIN AND PROSTACYCLIN ANALOGS
COLLINS, PW
DJURIC, SW
[J]. CHEMICAL REVIEWS, 1993, 93 (04) : 1533 - 1564
[7] A new chemoenzymatic approach to the synthesis of Latanoprost and Bimatoprost
Contente, Martina Letizia
Zambelli, Paolo
Galafassi, Silvia
Tamborini, Lucia
Pinto, Andrea
Conti, Paola
Molinari, Francesco
Romano, Diego
[J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2015, 114 : 7 - 12
[8] STEREO-CONTROLLED SYNTHESIS OF PROSTAGLANDINS F2ALPHA AND E2 (DL)
COREY, EJ
WEINSHENKER, NM
SCHAAF, TK
HUBER, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (20) : 5675 - +
[9] Stereocontrolled organocatalytic synthesis of prostaglandin PGF2α in seven steps
Coulthard, Graeme
Erb, William
Aggarwal, Varinder K.
[J]. NATURE, 2012, 489 (7415) : 278 - 281
[10] Dams I., 2013, PROSTAG OTH LIPID M, P109

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