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Digitale Medien

A Practical Synthesis of the Cyclohexyl Part of the Immunosuppressant FK506 (1998)

Haller, Bernd-Uwe ; Kruber, Susanne ; Maier, Martin E.

New York, NY : Wiley-Blackwell

Journal für Praktische Chemie/Chemiker-Zeitung 340 (1998), S. 656-661

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Details

ISSN: 0941-1216

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Starting from the benzylidene lactone 3 of D-(-)-quinic acid the cyclohexyl fragment 15 (C-28-C-34 part) of the immunosuppressant FK506 was synthesized. Key steps include homolytic deoxygenation reactions on compounds 4 and 6 as well as a regioselective opening of the benzylidene acetal 5. Opening of the lactone 7 to provide the methyl ester 8 was followed by methylation of the hydroxy group to give 9. Further steps provided the aldehyde 12 which was elongated to the alkyne 15. This sequence provides 15 in gram quantities.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/prac.19983400710

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