Synthetic studies on lactonamycins: Synthesis of the model BCDEF aglycon

Kana Watanabe, Yusuke Iwata, Satoshi Adachi, Tomoyuki Nishikawa, Yuko Yoshida, Shunsuke Kameda, Mitsuaki Ide, Yoko Saikawa, Masaya Nakata

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

The lactonamycin model aglycon 4 was synthesized from the trihalogenated benzene derivative 10. Ethynyltetraol 6 was prepared from 10 via carbon elongations, oxidative demethylation, a cycloaddition reaction with the diene derived from homophthalic anhydride, and dihydroxylation. Final E- and F-ring constructions from 6 were realized via a palladium-catalyzed cyclization-methoxycarbonylation, a stereoselective methanol addition, and lactonization, leading to the production of 4.

Original languageEnglish
Pages (from-to)5573-5579
Number of pages7
JournalJournal of Organic Chemistry
Volume75
Issue number16
DOIs
Publication statusPublished - 2010 Aug 20

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthetic studies on lactonamycins: Synthesis of the model BCDEF aglycon'. Together they form a unique fingerprint.

  • Cite this

    Watanabe, K., Iwata, Y., Adachi, S., Nishikawa, T., Yoshida, Y., Kameda, S., Ide, M., Saikawa, Y., & Nakata, M. (2010). Synthetic studies on lactonamycins: Synthesis of the model BCDEF aglycon. Journal of Organic Chemistry, 75(16), 5573-5579. https://doi.org/10.1021/jo100913s