Unexpected Diels-Alder/carbonyl-ene cascade toward the biomimetic synthesis of chloropupukeananin.

Takahiro Suzuki, Yuria Miyajima, Kaname Suzuki, Kanako Iwakiri, Masaki Koshimizu, Go Hirai, Mikiko Sodeoka, Susumu Kobayashi

Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.

Organic letters 2013 Apr 5

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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.

Citation

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