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  • Title: Enantioselective Total Synthesis of (-)-Hamigeran F and Its Rearrangement Product.
    Author: Xiong Y, Chen YH, Li T, Xie JH, Zhou QL.
    Journal: Org Lett; 2022 Jul 22; 24(28):5161-5165. PubMed ID: 35816023.
    Abstract:
    Herein, we report the first enantioselective total synthesis of the highly complex hamigeran diterpenoid (-)-hamigeran F and its rearrangement product. The synthetic strategy features key steps of asymmetric hydrogenation, Horner-Wadsworth-Emmons olefination, and intramolecular Friedel-Crafts acylation to construct the [6,6,5]-tricyclic skeleton bearing three consecutive stereocenters, a sequence of steps involving Rosenmund reduction, Wittig reaction, dihydroxylation to assemble the α-acetoxy ketone group, and an intramolecular aldol reaction to build the tetracyclic core structure.
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