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  • Title: Exceedingly Concise and Elegant Synthesis of (+)-Paniculatine, (-)-Magellanine, and (+)-Magellaninone.
    Author: Lin KW, Ananthan B, Tseng SF, Yan TH.
    Journal: Org Lett; 2015 Aug 07; 17(15):3938-40. PubMed ID: 26207328.
    Abstract:
    Starting from inexpensive (+)-pulegone as the chiral building block, a highly convergent synthesis of the unusual diquinane-based structures of (+)-paniculatine (1), (-)-magellanine (2), and (+)-magellaninone (3), has been achieved. This approach is based upon a tandem acylation-alkylation of ketoester 8 and palladium-catalyzed olefin insertion, oxidation, and hydrogenation for construction of the tetracyclic framework. This exceedingly concise strategy, requiring only 12-14 steps, is the shortest to date.
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