Total Synthesis of Lucidumone through Convenient One-pot Preparation of the Tetracyclic Skeleton by Claisen Rearrangement and Subsequent Intramolecular Aldol Reaction |
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Authors: | Dr. Yuichiro Kawamoto Naoki Noguchi Dr. Toyoharu Kobayashi Prof. Hisanaka Ito |
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Affiliation: | School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392 Japan |
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Abstract: | The total synthesis of lucidumone ( 1 ), a Ganoderma meroterpenoid, was accomplished in racemic form from easily prepared 6 and 7 in 10 steps as the longest linear sequence. The synthesis was completed through one-pot preparation of the tetracyclic core skeleton by Claisen rearrangement followed by an intramolecular aldol reaction. The intramolecular aldol reaction allowed for the stereocontrolled construction of the bicyclo [2.2.2] octane skeleton fused to an indanone structure. The enantioselective total synthesis of 1 was also described via a chiral transfer strategy in the Claisen rearrangement. |
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Keywords: | Aldol Reaction Chiral Transfer Claisen Rearrangement Sequential Transformation Total Synthesis |
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