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  • Title: Collective total synthesis of tetracyclic diquinane Lycopodium alkaloids (+)-paniculatine, (-)-magellanine, (+)-magellaninone and analogues thereof.
    Author: Jiang SZ, Lei T, Wei K, Yang YR.
    Journal: Org Lett; 2014 Nov 07; 16(21):5612-5. PubMed ID: 25299586.
    Abstract:
    The collective total synthesis of tetracyclic diquinane Lycopodium alkaloids, (+)-paniculatine, (-)-magellanine, (+)-magellaninone, and two analogues (-)-13-epi-paniculatine and (+)-3-hydroxyl-13-dehydro-paniculatine, has been accomplished. By logic-guided addition of a strategically useful hydroxyl group at C-3 of paniculatine, the formidable tetracyclic core was rapidly synthesized utilizing a site-specific and stereoselective aldol cyclization, thus making the ABD → ABCD tetracyclic approach to diquinane Lycopodium alkaloids attainable for the first time.
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