Abstract
Total syntheses of (−)-plectrodorine [(−)- 1] and (+)-oxerine [(+)- 3] possessing the cyclopenta[ c]pyridine ring system have been accomplished through a route starting from the chiral γ-butyrolactone 7 and exploiting the intramolecular oxazole–olefin Diels–Alder reaction. The sign of specific rotation for the synthetic (+)- 3 was in disagreement with that reported for natural oxerine, leaving the absolute configuration of this monoterpene alkaloid incomplete.
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