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Unified Approach toward Syntheses of Juglomycins and Their Derivatives.

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.

SUBMITTER: Yoshioka K

PROVIDER: S-EPMC6682012 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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Unified Approach toward Syntheses of Juglomycins and Their Derivatives.

Yoshioka Kai K Kamo Shogo S Hosaka Keisuke K Sato Ryohei R Miikeda Yuma Y Manabe Yuri Y Tomoshige Shusuke S Tsubaki Kazunori K Kuramochi Kouji K

ACS omega 20190705 7

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 3<i>R</i>,4<i>R</i> t ...[more]

PMID: 31460280

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