@article{037ec43e814f486a9b94e961ee643a03,
title = "Bioinspired total synthesis of boneratamides A-C",
abstract = "We disclose the first synthesis of the marine natural product, (+)-boneratamide A, whose structure is composed of a terpene unit linked via an amide bond to a pyroglutamic acid moiety. The key step in this route is a bioinspired Ugi reaction of (+)-axisonitrile-3 with acetone as the carbonyl component and l-glutamic acid. This reaction brings about a remarkably efficient, one-pot assembly of reaction components concomitant with γ-lactam ring formation to produce (+)-boneratamide A in 70% yield. (+)-Boneratamide B and (-)-boneratamide C methyl esters were also synthesized using a similar bioinspired strategy, and the relative stereochemistries at the stereogenic centers in these substances were elucidated using X-ray analysis.",
author = "Kaito Ooka and Keisuke Nakanishi and Yutaro Udagawa and Yoshiyasu Ichikawa and Seijiro Hosokawa",
note = "Funding Information: We are most grateful to Professor Raymond J. Andersen (University of British Columbia) for generously providing us with the original NMR spectroscopic data of boneratamide A-C methyl esters and for helpful discussions and useful suggestions. The Materials Characterization Central Laboratory at Waseda University and the MEXT Project (JPMXS0440500022) are gratefully acknowledged for X-ray analysis. Generous financial support provided by a Grant-in-Aid for Scientific Research (C) (16K01916) from MEXT is gratefully acknowledged. Funding Information: We are most grateful to Professor Raymond J. Andersen (University of British Columbia) for generously providing us with the original NMR spectroscopic data of boneratamide A–C methyl esters and for helpful discussions and useful suggestions. The Materials Characterization Central Laboratory at Waseda University and the MEXT Project (JPMXS0440500022) are gratefully acknowledged for X-ray analysis. Generous financial support provided by a Grant-in-Aid for Scientific Research (C) (16K01916) from MEXT is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",
year = "2022",
month = sep,
day = "24",
doi = "10.1039/d2ob00486k",
language = "English",
volume = "20",
pages = "8236--8242",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "42",
}