Use of the oxazole-olefin Diels-Alder reaction in the total synthesis of the monoterpene alkaloids (-)-plectrodorine and (+)-oxerine

概要

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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 γ-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. © 2006 Pharmaceutical Society of Japan.
公益社団法人日本薬学会の論文
2006-01-01