Sign in to use this feature.

Years

Between: -

Subjects

remove_circle_outline
remove_circle_outline

Journals

Article Types

Countries / Regions

Search Results (2)

Search Parameters:
Keywords = Julia–Lythgoe olefination

Order results
Result details
Results per page
Select all
Export citation of selected articles as:
16 pages, 1336 KiB  
Article
A Novel Convergent Synthesis of the Potent Antiglaucoma Agent Tafluprost
by Małgorzata Krupa, Michał Chodyński, Anna Ostaszewska, Piotr Cmoch and Iwona Dams
Molecules 2017, 22(2), 217; https://doi.org/10.3390/molecules22020217 - 31 Jan 2017
Cited by 14 | Viewed by 9006
Abstract
Tafluprost (AFP-168, 5) is a unique 15-deoxy-15,15-difluoro-16-phenoxy prostaglandin F2α (PGF2α) analog used as an efficacious ocular hypotensive agent in the treatment of glaucoma and ocular hypertension, as monotherapy, or as adjunctive therapy to β-blockers. A novel convergent synthesis of 5 was developed employing [...] Read more.
Tafluprost (AFP-168, 5) is a unique 15-deoxy-15,15-difluoro-16-phenoxy prostaglandin F2α (PGF2α) analog used as an efficacious ocular hypotensive agent in the treatment of glaucoma and ocular hypertension, as monotherapy, or as adjunctive therapy to β-blockers. A novel convergent synthesis of 5 was developed employing Julia–Lythgoe olefination of the structurally advanced prostaglandin phenylsulfone 16, also successfully applied for manufacturing of pharmaceutical grade latanoprost (2), travoprost (3) and bimatoprost (4), with an aldehyde ω-chain synthon 17. The use of the same prostaglandin phenylsulfone 16, as a starting material in parallel syntheses of all commercially available antiglaucoma PGF2α analogs 2–5, significantly reduces manufacturing costs resulting from its synthesis on an industrial scale and development of technological documentation. Another key aspect of the route developed is deoxydifluorination of a trans-13,14-en-15-one 30 with Deoxo-Fluor. Subsequent hydrolysis of protecting groups and final esterification of acid 6 yielded tafluprost (5). The main advantages are the preparation of high purity tafluprost (5) and the application of comparatively cheap reagents. The preparation and identification of two other tafluprost acid derivatives, tafluprost methyl ester (32) and tafluprost ethyl amide (33), are also described. Full article
(This article belongs to the Section Medicinal Chemistry)
Show Figures

Graphical abstract

6 pages, 64 KiB  
Article
Application of the Solid-Phase Julia–Lythgoe Olefination in Vitamin D Side-Chain Construction
by Jo N. D'herde and Pierre J. De Clercq
Molecules 2006, 11(8), 655-660; https://doi.org/10.3390/11080655 - 26 Aug 2006
Cited by 6 | Viewed by 8132
Abstract
An example of the Julia–Lythgoe attachment of the vitamin D side chain to a solid-phase linked Inhoffen–Lythgoe diol derived CD-ring fragment is reported. Full article
Show Figures

Figure 1

Back to TopTop