Publication detail

Alternative Approaches to Alfaprostol Intermediate Using Corey Lactone Alkyne

Authors: Agostinho Monteiro Sara Eunice | Imramovský Aleš | Pauk Karel | Pavelová Radka | Pavlík Jan

Year: 2019

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	Alternative Approaches to Alfaprostol Intermediate Using Corey Lactone Alkyne	Prostaglandins are a group of lipid mediators with multiple pharmaceutical and veterinary applications. Their synthesis includes a complex multi-step pathway with over 20 steps and high associated productions costs. Alfaprostol is a nonhalogenated synthetic PGF2α methyl ester analogue with veterinary application as luteolytic agent. Literature described two main methodologies for preparation of optically active propargylic alcohols, namely: asymmetric reduction of a propargylic ketone or the asymmetric alkynylation of a carbonyl group.2 Our group is currently targeting efforts in the development of a new synthetic approach for the synthesis of alfaprostol ω-chain. In this context the two previously mentioned methodologies were studied and applied to target molecule. Stille coupling has been successfully used to afford propargylic ketone susceptible of asymmetric reduction. Presently we are focusing our effort on the direct preparation of propargylic alcohol with adequate stereoselectivity using Corey lactone bromoalkyne and 3-cyclohexylpropanal as starting materials. Corey lactone bromoalkyne has been prepared from Corey lactone aldehyde provided by Cayman Pharma ltd.. Two different strategies have been developed for the preparation of this crucial intermediate.	Alfaprostol; Corey lactone; assymetric alkynylation; Stille coupling

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