TY - JOUR
T1 - Unified Approach toward Syntheses of Juglomycins and Their Derivatives
AU - Yoshioka, Kai
AU - Kamo, Shogo
AU - Hosaka, Keisuke
AU - Sato, Ryohei
AU - Miikeda, Yuma
AU - Manabe, Yuri
AU - Tomoshige, Shusuke
AU - Tsubaki, Kazunori
AU - Kuramochi, Kouji
N1 - Funding Information:
This study was partly supported by a Grant-in Aid from the Japan Society for the Promotion of Science (JSPS) Fellows (no. 16J00542) to S.K. and a Grant-in-Aid for Scientific Research (C) (KAKENHI no. 15K07416) and the Sumitomo Foundation (no. 170183) to K.K.
Publisher Copyright:
Copyright © 2019 American Chemical Society.
PY - 2019/7/31
Y1 - 2019/7/31
N2 - 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.
AB - 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.
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U2 - 10.1021/acsomega.9b01376
DO - 10.1021/acsomega.9b01376
M3 - Article
AN - SCOPUS:85078774997
VL - 4
SP - 11737
EP - 11748
JO - ACS Omega
JF - ACS Omega
SN - 2470-1343
IS - 7
ER -