Enantioselective total synthesis of isishippuric acid B via intramolecular Michael reaction |
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| Authors: | Torihata Munefumi Nakahata Takashi Kuwahara Shigefumi |
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| Affiliation: | Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Aoba-ku, Sendai 981-8555, Japan. |
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| Abstract: | The first enantioselective total synthesis of isishippuric acid B bearing a novel 4,5-seco-6-norquadrane skeleton was accomplished from (R)-citronellal with use of a Diels-Alder cycloaddition and an intramolecular Michael addition as the ring-forming steps. Comparison of the optical rotation of the synthetic material with that of the natural product confirmed the absolute configuration of isishippuric acid B to be 1R, 2R, 8R, and 11R. |
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