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• W2950061750 endingPage "9667" @default.
• W2950061750 startingPage "9653" @default.
• W2950061750 abstract "An asymmetric synthesis of the anti-metastatic prostacyclin analogue cicaprost and a formal one of its isomer isocicaprost by a new route are described. A key step of these syntheses is the coupling of a chiral bicyclic C6-C14 ethynyl building block with a chiral C15-C21 omega-side chain amide building block with formation of the C14-C15 bond of the target molecules. A highly stereoselective reduction of the thereby obtained C6-C21 intermediate carrying a carbonyl group at C15 of the side chain was accomplished by the chiral oxazaborolidine method. The chiral phosphono acetate method was used for the highly stereoselective attachment of the alpha-side chain to the bicyclic C6-C21 intermediate carrying a carbonyl group at C6. Asymmetric syntheses of the bicyclic C6-C14 ethynyl building blocks were carried out starting from achiral bicyclic C6-C12 ketones by using the chiral lithium amide method. In the course of these syntheses, a new method for the introduction of an ethynyl group at the alpha-position of the carbonyl group of a ketone with formation of the corresponding homopropargylic alcohol was devised. Its key steps are an aldol reaction of the corresponding silyl enol ether with chloral and the elimination of a trichlorocarbinol derivative with formation of the ethynyl group. In addition, a new aldehyde to terminal alkyne transformation has been realized. Its key steps are the conversion of an aldehyde to the corresponding 1-alkenyl dimethylaminosulfoxonium salt and the elimination of the latter with a strong base. Two basically different routes have been followed for the synthesis of the enantiomerically pure C15-C21 omega-side chain amide building block. The first is based on the chiral oxazolidinone method and features a highly stereoselective alkylation of (4R)-N-acetyl-4-benzyloxazolidin-2-one, and the second encompasses a malonate synthesis of the racemic amide and its efficient preparative scale resolution by HPLC on a chiral stationary phase containing column." @default.
• W2950061750 created "2019-06-27" @default.
• W2950061750 creator A5013983266 @default.
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• W2950061750 creator A5088107347 @default.
• W2950061750 date "2003-07-19" @default.
• W2950061750 modified "2023-09-23" @default.
• W2950061750 title "Asymmetric Synthesis of the Highly Potent Anti-Metastatic Prostacyclin Analogue Cicaprost and Its Isomer Isocicaprost" @default.
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• W2950061750 doi "https://doi.org/10.1021/ja030200l" @default.
• W2950061750 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/12904032" @default.
• W2950061750 hasPublicationYear "2003" @default.
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