Chiral synthons from carvone. Part 50. Enantiospecific approaches to both enantiomers of bicyclo[4.3.0]nonane-3,8-dione derivatives
作者： A. Srikrishna , T. Jagadeeswar Reddy
DOI: 10.1039/B104253J
关键词: Ketone 、 Regioselectivity 、 Cyclopropanation 、 Stereochemistry 、 Claisen rearrangement 、 Bicyclic molecule 、 Enone 、 Chemistry 、 Diazo 、 Cyclopropane
摘要: Enantiospecific synthesis of both enantiomeric forms bicyclo[4.3.0]nonane-3,8-dione derivatives has been described starting from (R)-carvone employing two different cyclopentannulation methodologies. Thus, in the first methodology, carveol (5) was converted into tricyclic ketone 4 a Claisen rearrangement and intramolecular diazo cyclopropanation reactions. Degradation isopropenyl group followed by cyclopropane cleavage cuprate addition generated dione (−)-12a. Whereas, Wacker mediated via 15 furnished enone 17. Functional manipulation including degradation transformed 17 into (+)-12a, which on regioselective ketalisation ketoketal (+)-2.
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