340181-93-3Relevant articles and documents
A unified strategy to prostaglandins: chemoenzymatic total synthesis of cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost guided by biocatalytic retrosynthesis
Chen, Fener,Huang, Zedu,Jiang, Meifen,Li, Weijian,Tang, Pei,Ye, Baijun,Zhang, Guo-Tai,Zhu, Kejie
, p. 10362 - 10370 (2021/08/16)
Development of efficient and stereoselective synthesis of prostaglandins (PGs) is of utmost importance, owing to their valuable medicinal applications and unique chemical structures. We report here a unified synthesis of PGs cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost from the readily available dichloro-containing bicyclic ketone6aguided by biocatalytic retrosynthesis, in 11-12 steps with 3.8-8.4% overall yields. An unprecedented Baeyer-Villiger monooxygenase (BVMO)-catalyzed stereoselective oxidation of6a(99% ee), and a ketoreductase (KRED)-catalyzed diastereoselective reduction of enones12(87?:?13 to 99?:?1 dr) were utilized in combination for the first time to set the critical stereochemical configurations under mild conditions. Another key transformation was the copper(ii)-catalyzed regioselectivep-phenylbenzoylation of the secondary alcohol of diol10(9.3?:?1 rr). This study not only provides an alternative route to the highly stereoselective synthesis of PGs, but also showcases the usefulness and great potential of biocatalysis in construction of complex molecules.
Novel method for preparing Prostaglandin derivatives
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Paragraph 0133; 0136; 0166-0168, (2017/10/31)
Provided is a novel method for preparing prostaglandin derivatives. The method is suitable for mass production by effectively manufacturing prostaglandin derivatives with high yield. The method comprises the following steps: (S-1) adding a first reducing agent to a prostaglandin intermediate compound represented by chemical formula II and manufacturing a compound represented by chemical formula III; (S-2) manufacturing a compound represented by chemical formula IV from the compound represented by chemical formula III in the presence of a base; (S-3) adding a second reducing agent to the compound represented by chemical formula IV and manufacturing a compound represented by chemical formula V; and (S-4) performing Wittig reaction of the compound represented by chemical formula V and a compound represented by chemical formula VI, and manufacturing a compound represented by chemical formula I.COPYRIGHT KIPO 2017
Processes for the preparation of isomer free prostaglandins
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Paragraph 0106, (2015/03/03)
Novel processes for the preparation of a compound of Formula I-2 substantially free of the 5,6-trans isomer: wherein R2, R3 and R4 are as defined in the specification are provided. Novel intermediates for the preparations of isomer free Prostaglandins and derivatives thereof are also provided.