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Use of the Oxazole-Olefin Diels-Alder Reaction in the Total Synthesis of the Monoterpene Alkaloids (-)-Plectrodorine and (+)-Oxerine

Accession number;06A0025401

Title;Use of the Oxazole-Olefin Diels-Alder Reaction in the Total Synthesis of the Monoterpene Alkaloids (-)-Plectrodorine and (+)-Oxerine

Author; OHBA MASASHI (Advanced Sci. Res. Center, Kanazawa Univ.) IZUTA RIE (Fac. Of Pharmaceutical Sciences, Kanazawa Univ.) SHIMIZU EMI (Fac. Of Pharmaceutical Sciences, Kanazawa Univ.)

Journal Title;Chem Pharm Bull

Journal Code:G0504A

ISSN:0009-2363

VOL.54;NO.1;PAGE.63-67 (J-STAGE)(2006)

Figure&Table&Reference;FIG.1, REF.43

Pub. Country;Japan

Language;English

Abstract;A full account of the total synthesis of two monoterpene alkaloids, (-)-plectrodorine [(-)-1] and (+)-oxerine [(+)-3], is presented. The key steps involved are the formation of the oxazole alcohol 10 from the .GAMMA.-butyrolactone 9 and the intramolecular Diels-Alder reaction of the oxazole-olefins 13a, b. Since the sign of specific rotation for the synthetic (+)-3 was different from that reported for natural oxerine, the absolute configuration of this alkaloid is not yet fully understood. (Author abst.)

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