Unified Approach toward Syntheses of Juglomycins and Their Derivatives

Kai Yoshioka, Shogo Kamo, Keisuke Hosaka, Ryohei Sato, Yuma Miikeda, Yuri Manabe, Shusuke Tomoshige, Kazunori Tsubaki, Kouji Kuramochi

Research output: Contribution to journalArticlepeer-review

Abstract

A unified and common intermediate strategy for syntheses of juglomycins and their derivatives is reported. The use of a 1,4-dimethoxynaphthalene derivative as a key intermediate enabled easy access to various juglomycin derivatives. In this study, juglomycins A-D, juglomycin C amide, khatmiamycin and its 4-epimer, and the structure proposed for juglomycin Z were synthesized from this intermediate. The absolute configuration of natural khatmiamycin has been established to be 3R,4R through our synthesis. Unfortunately, the spectroscopic data for synthetic juglomycin Z were not consistent with the data reported for the natural one, strongly suggesting a structural misassignment.

Original languageEnglish
Pages (from-to)11737-11748
Number of pages12
JournalACS Omega
Volume4
Issue number7
DOIs
Publication statusPublished - 2019 Jul 31

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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