913258-20-5Relevant articles and documents
A new synthetic approach to high-purity (15R)-latanoprost
Martynow, Jacek G.,Jozwik, Julita,Szelejewski, Wieslaw,Achmatowicz, Osman,Kutner, Andrzej,Wisniewski, Krzysztof,Winiarski, Jerzy,Zegrocka-Stendel, Oliwia,Golebiewski, Piotr
, p. 689 - 703 (2007/10/03)
This paper describes a new synthesis of latanoprost (1) that afforded high purity latanoprost in 16.9 % overall yield in eight synthetic steps from sulfone 4. The "a chain" in a derivative of the (-)-"Corey lactone" was elongated first, followed by the attachment of a novel, enantiomerically pure "ω chain" synthon. This ensured the absence of the undesired (15S)-1 diastereomer in the synthesized prostaglandin. The crystalline nature of the novel sulfone 4 facilitated its purification. A variation of the new synthesis of latanoprost is described, where the laboratory-scale synthesis was further adapted to a hundred-gram scale. In the course of the present synthesis, a new prostaglandin sulfone intermediate, 21, which may find application in the synthesis of diverse prostaglandin analogs, was introduced. A practical synthesis of novel, enantiomerically pure "ω chain" synthons 15, 16, and 17 has also been carried out, employing diol 12, which was obtained from derivatives of the D-mannitol chiral pool. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.