551-11-1Relevant articles and documents
Marnett,Bienkowski
, p. 4303,4304 - 4307 (1977)
Concise, scalable and enantioselective total synthesis of prostaglandins
Zhang, Fuhao,Zeng, Jingwen,Gao, Mohan,Wang, Linzhou,Chen, Gen-Qiang,Lu, Yixin,Zhang, Xumu
, p. 692 - 697 (2021/06/01)
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.]
Access to a Key Building Block for the Prostaglandin Family via Stereocontrolled Organocatalytic Baeyer–Villiger Oxidation
Zhu, Kejie,Hu, Sha,Liu, Minjie,Peng, Haihui,Chen, Fen-Er
, p. 9923 - 9927 (2019/05/16)
A new protocol for the construction of a crucial bicyclic lactone of prostaglandins using a stereocontrolled organocatalytic Baeyer–Villiger (B-V) oxidation was developed. The key B-V oxidation of a racemic cyclobutanone derivative with aqueous hydrogen peroxide has enabled an early-stage construction of a bicyclic lactone skeleton in high enantiomeric excess (up to 95 %). The generated bicyclic lactone is fully primed with two desired stereocenters and enabled the synthesis of the entire family of prostaglandins according to Corey′s route. Furthermore, the reactivity and enantioselectivity of B-V oxidation of racemic bicyclic cyclobutanones were evaluated and 90–99 % ee was obtained, representing one of the most efficient routes to chiral lactones. This study further facilitates the synthesis of prostaglandins and chiral lactone-containing natural products to promote drug discovery.
Of the trometamol prostaglandin F2 α synthesis method (by machine translation)
-
, (2017/08/30)
The invention discloses a of the trometamol prostaglandin F2 α synthesis method, as the compound (-) - Corey lactone diol as raw materials, through the oxidation reaction to obtain lactone aldehyde, lactone aldehydechain after the weidiWeidi Greecehuo Naer reaction with - the lower side of the splicing an olefin, the olefin double-carbonyl after reduction to obtain the alcohol, with puncture ylide - wittich reaction the upper side of the obtained prostaglandin F2 α, then the prostaglandin F2 α of the trometamol after crystallization by dissolving of the trometamol prostaglandin F2 α. The synthesis method, without noble metal catalyst, there is little side reaction, high yield, low cost, less pollution, is suitable for industrial production. (by machine translation)