Total synthesis of the antibiotic kendomycin: A macrocyclization using the Tsuji-Trost etherification

Tetsuya Sengoku, Shu Xu, Kenji Ogura, Yoshinori Emori, Kenji Kitada, Daisuke Uemura, Hirokazu Arimoto

    Research output: Contribution to journalArticle

    14 Citations (Scopus)

    Abstract

    A highly stereocontrolled, convergent total synthesis of kendomycin [(-)-TAN2162], an ansa-macrocyclic antibiotic, is reported. The key of the strategy is an unprecedented Tsuji-Trost macrocyclic etherification, followed by a transannular Claisen rearrangement to construct the 18-membered carbocyclic framework. The oxa-six- and five-membered rings were also stereoselectively constructed respectively by a cascade oxidative cyclization at an unfunctionalized benzylic position and using a one-pot epoxidation/5-exo-tet epoxide opening. A new construct: The asymmetric total synthesis of the antibiotic kendomycin was accomplished by using a highly stereocontrolled convergent route. The key feature of the synthetic strategy is the construction of an 18-membered carbocycle based on an intramolecular Tsuji-Trost etherification/transannular Claisen rearrangement sequence. TBS=tert- butyldimethylsilyl.

    Original languageEnglish
    Pages (from-to)4213-4216
    Number of pages4
    JournalAngewandte Chemie - International Edition
    Volume53
    Issue number16
    DOIs
    Publication statusPublished - 2014 Apr 14

    Keywords

    • antibiotics
    • macrocycles
    • natural products
    • palladium
    • total synthesis

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)

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