Studies on Biomimetic Synthesis of Chloropupukeananin under High-Pressure Conditions and Investigation into High-Pressure Effect in the Diels-Alder reaction

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We have developed the effective synthesis of a bioactive natural product, chloropupukeananin. Since chloropupukeananin possesses a highly-functionalized complex structure, we planned the biomimetic synthesis of chloropupukeananin. Using, chiral vinylallene and MOB as model compounds of biosynthetic precursors, we have achieved the synthesis of model compound of chloropupukeananin by a Diels-Alder/carbonyl-ene reaction cascade under high-pressure conditions and migration of an acyl group. We have also synthesized the key intermediate and fragments of biosynthetic precursors. We have studied the high-pressure Diels-Alder reaction of the biosynthetic intermediate of Lovastatin for the investigation into high-pressure effect in biosynthesis.