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The biomimetic synthesis of the advanced model compound of chloropupukeananin has been achieved. The present synthesis features an unexpected enantiomer-differentiating Diels-Alder/carbonyl-ene cascade under high-pressure conditions and a base-promoted migration of the salicyl group.


Takahiro Suzuki, Yuria Miyajima, Kaname Suzuki, Kanako Iwakiri, Masaki Koshimizu, Go Hirai, Mikiko Sodeoka, Susumu Kobayashi. Unexpected Diels-Alder/carbonyl-ene cascade toward the biomimetic synthesis of chloropupukeananin. Organic letters. 2013 Apr 5;15(7):1748-51

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PMID: 23530662

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