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 journalArticlepeer-review

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

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