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  • Title: Unified Total Synthesis of Madangamines A, C, and E.
    Author: Suto T, Yanagita Y, Nagashima Y, Takikawa S, Kurosu Y, Matsuo N, Sato T, Chida N.
    Journal: J Am Chem Soc; 2017 Mar 01; 139(8):2952-2955. PubMed ID: 28190360.
    Abstract:
    A stereodivergent strategy for the synthesis of skipped dienes is developed. The method consists of hydroboration of allenes and Migita-Kosugi-Stille coupling, which allows for access to all four possible stereoisomers of the skipped dienes. The hydroboration is especially useful for providing both E-allylic and Z-allylic alcohols from the same allene by simply changing the organoborane reagent. The strategy was successfully applied to a unified total synthesis of the madangamine alkaloids via a common ABCE-tetracyclic intermediate with a (Z,Z)-skipped diene. The late-stage variation of the D-ring enabled the supply of synthetic madangamines A, C, and E for the first time.
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