TY - JOUR
T1 - Total synthesis of exigurin
T2 - The Ugi reaction in a hypothetical biosynthesis of natural products
AU - Hosokawa, Seijiro
AU - Nakanishi, Keisuke
AU - Udagawa, Yutaro
AU - Maeda, Mitsutoshi
AU - Sato, Seiya
AU - Nakano, Keiji
AU - Masuda, Toshiya
AU - Ichikawa, Yoshiyasu
N1 - Funding Information:
We are most grateful to Professor Shinji Ohta (Hiroshima University) for kindly providing us the NMR spectral data of exiguamide (21), (−)-10-epi-axisonitrile-3 (3) and exigurin (1). The Materials Characterization Central Laboratory at Waseda University is gratefully acknowledged for X-ray analysis. We acknowledge the financial support provided by a Grant-in-Aid for Scientific Research (C) (16K01916) from the MEXT.
Publisher Copyright:
This journal is © The Royal Society of Chemistry.
PY - 2020
Y1 - 2020
N2 - The first total synthesis of a marine natural product, exigurin, has been accomplished in 13 steps starting from (+)-menthone. The key intermediate (-)-10-epi-axisonitrile-3 was prepared by stereoselective intramolecular cyclopropanation followed by a cyclopropane ring opening reaction by the azide anion. The bioinspired Ugi reaction of (-)-10-epi-axisonitrile-3, formaldehyde, sarcosine and methanol successfully constructed the target exigurin in which its terpene and amino acid units were linked through an amide bond.
AB - The first total synthesis of a marine natural product, exigurin, has been accomplished in 13 steps starting from (+)-menthone. The key intermediate (-)-10-epi-axisonitrile-3 was prepared by stereoselective intramolecular cyclopropanation followed by a cyclopropane ring opening reaction by the azide anion. The bioinspired Ugi reaction of (-)-10-epi-axisonitrile-3, formaldehyde, sarcosine and methanol successfully constructed the target exigurin in which its terpene and amino acid units were linked through an amide bond.
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U2 - 10.1039/c9ob02249j
DO - 10.1039/c9ob02249j
M3 - Article
C2 - 31903473
AN - SCOPUS:85078685138
SN - 1477-0520
VL - 18
SP - 687
EP - 693
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 4
ER -
