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

19 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

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Benzene Derivatives
Cycloaddition
Anhydrides
Cyclization
Palladium
Methanol
Elongation
Carbon
lactonamycin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Watanabe, K., Iwata, Y., Adachi, S., Nishikawa, T., Yoshida, Y., Kameda, S., ... 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

Synthetic studies on lactonamycins : Synthesis of the model BCDEF aglycon. / Watanabe, Kana; Iwata, Yusuke; Adachi, Satoshi; Nishikawa, Tomoyuki; Yoshida, Yuko; Kameda, Shunsuke; Ide, Mitsuaki; Saikawa, Yoko; Nakata, Masaya.

In: Journal of Organic Chemistry, Vol. 75, No. 16, 20.08.2010, p. 5573-5579.

Research output: Contribution to journalArticle

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, vol. 75, no. 16, pp. 5573-5579. https://doi.org/10.1021/jo100913s
Watanabe K, Iwata Y, Adachi S, Nishikawa T, Yoshida Y, Kameda S et al. Synthetic studies on lactonamycins: Synthesis of the model BCDEF aglycon. Journal of Organic Chemistry. 2010 Aug 20;75(16):5573-5579. https://doi.org/10.1021/jo100913s
Watanabe, Kana ; Iwata, Yusuke ; Adachi, Satoshi ; Nishikawa, Tomoyuki ; Yoshida, Yuko ; Kameda, Shunsuke ; Ide, Mitsuaki ; Saikawa, Yoko ; Nakata, Masaya. / Synthetic studies on lactonamycins : Synthesis of the model BCDEF aglycon. In: Journal of Organic Chemistry. 2010 ; Vol. 75, No. 16. pp. 5573-5579.
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