Organic Letters
Letter
(16) Treatment of the equivalent of 3, possessing methyl ether
instead of isopropyl ether, with BCl3 at − 78 °C did not give the
corresponding cyclized product through the intramolecular Michael
addition and afforded the recovered starting material, quantitatively.
This result indicates that deprotection of alkyl ether under the
conditions would be a key for the initiation of the reaction.
(17) Trost, B. M.; Shen, H. C.; Surivet, J. P. Angew. Chem., Int. Ed.
2003, 42, 3943−3947.
Pharmacy, Kitasato University, Minato-ku, Tokyo 108-8641,
Japan
Shiho Arima − Laboratory of Synthetic Natural Products
Chemistry and Medicinal Research Laboratories, School of
Pharmacy, Kitasato University, Minato-ku, Tokyo 108-8641,
Japan
Takashi Fukuda − Laboratory of Aquatic Food Science,
Department of Fisheries, Faculty of Agriculture, Kindai
University, Nara 631-8505, Japan
Ryuji Uchida − Faculty of Pharmaceutical Sciences, Tohoku
Medical and Pharmaceutical University, Nara 631-8505, Japan
Hiroshi Tomoda − Laboratory of Microbial Chemistry and
Medicinal Research Laboratories, School of Pharmacy, Kitasato
University, Minato-ku, Tokyo 108-8641, Japan; orcid.org/
́
(18) Barrero, A. F.; Quílez del Moral, J. F.; Sanchez, E. M.; Arteaga,
J. F. Eur. J. Org. Chem. 2006, 2006, 1627−1641.
(19) Kuchkova, K. I.; Aricu, A. N.; Dragalin, I. P.; Vlad, P. F. Russ.
Chem. Bull. 2004, 53, 2862−2865.
(20) Kamishima, T.; Kikuchi, T.; Narita, K.; Katoh, T. Eur. J. Org.
Chem. 2014, 2014, 3443−3450.
(21) Gansauer, A.; Bluhm, H.; Pierobon, M. J. Am. Chem. Soc. 1998,
120, 12849−12859.
(22) Justicia, J.; Rosales, A.; Bunuel, E.; Oller-Lopez, J. L.; Valdivia,
M.; Haidour, A.; Oltra, J. E.; Barrero, A. F.; Cardenas, D. J.; Cuerva, J.
M. Chem. -Eur. J. 2004, 10, 1778−1788.
Complete contact information is available at:
(23) The stereochemistry was confirmed by NOE and ROESY
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was supported by a Grant-in-Aid for Scientific
Research (C) and a Kitasato University research grant for
young researchers (T.N.). We also thank Ms. N. Sato and Dr.
K. Nagai (Kitasato University) for kindly measuring NMR and
MS spectra.
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(13) The enantiomeric excess of 8 was determined by HPLC
analysis after amidation with (R)-(+)-1-phenylethyl amine; also see
(14) The stereochemistry was confirmed by NOE and ROESY
D
Org. Lett. XXXX, XXX, XXX−XXX