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Deprecated: Implicit conversion from float 211.6 to int loses precision in C:\Inetpub\vhosts\kidney.de\httpdocs\pget.php on line 534 J+Org+Chem 2014 ; 79 (19): 9402-7 Nephropedia Template TP
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Annulation Reactions of Allenyl Esters: An Approach to Bicyclic Diones and Medium-Sized Rings #MMPMID25184784
J Org Chem 2014[Oct]; 79 (19): 9402-7 PMID25184784show ga
A flexible approach to construct sterically congested bicyclo-alkenedione frameworks is reported. Under the action of potassium carbonate, ?-sulphonyl cycloalkanones are added to functionalized allenyl esters, leading to a lactone intermediate that is subsequently reduced to initiate an intramolecular aldol cyclization to [3.2.1], [3.3.1], and [4.3.1] bicycles. Oxidation then affords bicyclic diones in good three-step yields. Under exceptionally mild conditions, these bicycles are converted to highly functionalized medium-sized rings through a Grob-type fragmentation.