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  • Title: Concise synthesis of the multiply oxygenated ABC-ring system of the dihydro-β-agarofurans.
    Author: Ishiyama T, Urabe D, Fujisawa H, Inoue M.
    Journal: Org Lett; 2013 Sep 06; 15(17):4488-91. PubMed ID: 23937168.
    Abstract:
    The multiply oxygenated ABC-ring system of the dihydro-β-agarofurans was synthesized by employing two highly stereoselective reactions. The quinidine-catalyzed Diels-Alder reaction between a chiral dienophile and 3-hydroxy-4-methyl-2-pyrone simultaneously installed the C2-stereogenic center and two contiguous tetrasubstituted carbon centers (C5 and C10) of the A-ring. After 12 additional transformations, the aldol reaction of the resulting spiral AC-ring cyclized the B-ring with stereoselective introduction of the C7- and C8-centers.
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