Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate

Sébastien Prévost; Karen Thai; Nina Schützenmeister; Graeme Coulthard; William Erb; Varinder K. Aggarwal

doi:10.1021/ol503520f

Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate

Sébastien Prévost
, Karen Thai
, Nina Schützenmeister
, Graeme Coulthard
, William Erb
, Varinder K. Aggarwal

University of Bristol

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

Résumé

Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF_2α, 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.

langue originale	Anglais
Pages (de - à)	504-507
Nombre de pages	4
journal	Organic Letters
Volume	17
Numéro de publication	3
Les DOIs	https://doi.org/10.1021/ol503520f
état	Publié - 6 févr. 2015
Modification externe	Oui

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10.1021/ol503520f

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title = "Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate",

abstract = "Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF2α, 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.",

author = "S{\'e}bastien Pr{\'e}vost and Karen Thai and Nina Sch{\"u}tzenmeister and Graeme Coulthard and William Erb and Aggarwal, \{Varinder K.\}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = feb,

day = "6",

doi = "10.1021/ol503520f",

language = "English",

volume = "17",

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journal = "Organic Letters",

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TY - JOUR

T1 - Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate

AU - Prévost, Sébastien

AU - Thai, Karen

AU - Schützenmeister, Nina

AU - Coulthard, Graeme

AU - Erb, William

AU - Aggarwal, Varinder K.

PY - 2015/2/6

Y1 - 2015/2/6

N2 - Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF2α, 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.

AB - Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF2α, 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.

U2 - 10.1021/ol503520f

DO - 10.1021/ol503520f

M3 - Article

C2 - 25582321

AN - SCOPUS:84922594721

SN - 1523-7060

VL - 17

SP - 504

EP - 507

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate

Résumé

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