Construction of spiro[5.5]undecanes containing a quaternary carbon atom adjacent to a spirocentre via an Ireland ester Claisen rearrangement and RCM reaction sequence. Total syntheses of (±)-α-chamigrene, (±)-β-chamigrene and (±)-laurencenone C |
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Authors: | A. Srikrishna B. Vasantha Lakshmi Manoj Mathews |
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Affiliation: | Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India |
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Abstract: | Starting from cyclohexanecarboxylic acid, a combination of an Ireland ester Claisen rearrangement and RCM reactions was exploited for an efficient construction of spiro[5.5]undecanes containing a quaternary carbon atom adjacent to the spirocentre and the methodology was extended to complete total syntheses of three chamigrenes. |
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