- Concise, scalable and enantioselective total synthesis of prostaglandins
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Prostaglandins are among the most important natural isolates owing to their broad range of bioactivities and unique structures. However, current methods for the synthesis of prostaglandins suffer from low yields and lengthy steps. Here, we report a practicability-oriented synthetic strategy for the enantioselective and divergent synthesis of prostaglandins. In this approach, the multiply substituted five-membered rings in prostaglandins were constructed via the key enyne cycloisomerization with excellent selectivity (>20:1 d.r., 98% e.e.). The crucial chiral centre on the scaffold of the prostaglandins was installed using the asymmetric hydrogenation method (up to 98% yield and 98% e.e.). From our versatile common intermediates, a series of prostaglandins and related drugs could be produced in two steps, and fluprostenol could be prepared on a 20-gram scale. [Figure not available: see fulltext.]
- Zhang, Fuhao,Zeng, Jingwen,Gao, Mohan,Wang, Linzhou,Chen, Gen-Qiang,Lu, Yixin,Zhang, Xumu
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p. 692 - 697
(2021/06/01)
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- Carboprost 15-site isomer separation method
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The invention discloses a carboprost 15-site isomer impurity separation technical method, and belongs to the technical field of pharmaceutical chemical separation. The method comprises the steps: carrying out PG protection on the compound B with the 15-site hydroxyl tertiary alcohol to obtain 15-site S-type carboprost D and 15-site R-type carboprost E (forming the 15-site hydroxyl tertiary alcohol compound C), and separating to obtain a pure product of the 15-site carboprost D or the 15-site carboprost E. On the basis, the invention also provides a method for preparing the carboprost series products, wherein the method is suitable for industrial amplification. According to the method, after proper protecting group derivation, the isomer can be separated by adopting common silica gel column chromatography, the operation is simple, the quality of the obtained product meets the requirement, the production cost is greatly reduced, and the comprehensive benefit of the product is improved.
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Paragraph 0021; 0035; 0041-0042; 0047-0049; 0054-0055
(2021/04/14)
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- Preparation method of prostaglandin analogue
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The invention discloses a preparation method of a prostaglandin analogue, the prostaglandin analogue is a compound shown as a formula 9, the specific synthetic route is as follows: reagents and raw materials used in the invention are available on the market, and the preparation method has the advantages of mild reaction conditions, simple operation, low energy consumption and cost, and high yield,and is suitable for industrial production.
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- Method for separating prostaglandin isomer (by machine translation)
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The invention belongs to the technical field of separation of known, compound isomers, and particularly discloses a method for separating and separating. a prostaglandin isomer, and the method, for C separating the prostaglandin, isomer by splitting, the chiral E hydroxyl group in the compound (I) according to the present invention. (by machine translation)
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Paragraph 0035; 0041-0043
(2020/02/19)
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- PROCESS FOR THE PREPARATION OF CARBOPROST AND ITS TROMETHAMINE SALT
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The subject of the invention is a novel process for the preparation of Carboprost tromethamine salt where alkylation the enone of the general formula (II) is carried out in the presence of a chiral auxiliary in aprotic solvent with a Grignard reagent. The methyl ester epimers of formula (VII) are separated by gravity silicagel chromatography and the salt formation is carried out by using solid tromethamine base.
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- IMPROVED METHOD FOR THE WITTIG REACTION IN THE PREPARATION OF CARBOPROST
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A process for the preparation of carboprost methyl ester (figure (10)).
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Page/Page column 16; 21
(2008/12/07)
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