85550-82-9Relevant articles and documents
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.
Synthesis of Alfaprostol and PGF2α through 1,4-Addition of an Alkyne to an Enal Intermediate as the Key Step
Baars, Hannah,Classen, Moritz J.,Aggarwal, Varinder K.
, p. 6008 - 6011 (2017/11/10)
The veterinary drug Alfaprostol and prostaglandin PGF2α have been synthesized in just nine steps. The strategy involved the conjugate addition of an alkyne to a bicyclic enal, available in three steps by a proline-catalyzed aldol reaction of succinaldehyde. In the case of Alfaprostol, this resulted in the shortest synthesis reported to date. For PGF2α, this approach improved our previous route by making the 1,4-addition and ozonolysis more operationally simple.
Of the trometamol prostaglandin F2 α synthesis method (by machine translation)
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, (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)
Compound And Method
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Paragraph 0416-0418, (2015/06/17)
A compound of formula (I): (I) wherein Y is, Z is OR10, NR11R11 SR11, S(0)R11 S02R11, R10 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, CO—R11, or a protecting group, and R11 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or alkoxyl; a process for making a compound of formula (I); and a process for making a prostaglandin or a prostaglandin analogue using a compound of formula (I). wherein Y is
COMPOUND AND METHOD
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Page/Page column 84; 85, (2014/01/08)
A compound of formula (I): (I) wherein Y is, Z is OR10, NR11R11 SR11, S(0)R11 S02R11, R10 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, CO-R11, or a protecting group, and R11 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or alkoxyl; a process for making a compound of formula (I); and a process for making a prostaglandin or a prostaglandin analogue using a compound of formula (I).
Enantio-complementary Total Asymmetric Syntheses of Prostaglandin E2 and Prostaglandin F2α
Davies, John,Roberts, Stanley M.,Reynolds, Derek P.,Newton, Roger F.
, p. 1317 - 1320 (2007/10/02)
The racemic ketone (6) was converted into the diastereoisomeric alcohols (7) and (8) using actively fermenting yeast.These alcohols were separated and converted into the bromohydrins (-)-(9) and (+)-(9).The bromohydrin (-)-(9) was converted into prostaglandin E2 (1) and prostaglandin F2α (2) by reaction of the chiral cuprate reagent (15) with the tricyclic ketone (10), while the bromohydrin (+)-(9) was converted into the prostaglandins by reaction of the epoxyacetal (11) with the same cuprate reagent (15).
Photolytic Conversion of Some Bicycloheptanones into 3-Hydroxy- or 3-Methoxy-2-oxabicyclooctan-2-ones
Newton, Roger F.,Reynolds, Derek P.,Crossland, Noelle M.,Kelly, David R.,Roberts, Stanley M.
, p. 1583 - 1586 (2007/10/02)
The ketones (1) and (7)-(9) gave the corresponding cyclic acetals (3), (4), and (12)-(17), respectively, on photolysis in methanol.Concurrent production of the alkenes (6) and (18)-(20) detracted from the potential synthetic utility of this process.However, photolysis of the ketones (8), (10), and (11) in aqueous tetrahydrofuran or aqueous acetonitrile led to a highly selective ring-expansion process, and consequently high yields of the corresponding γ-lactols (21)-(23).
