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Paper | Special issue | Vol 95, No. 1, 2017, pp.422-444
Published online, 31st October, 2016
DOI: 10.3987/COM-16-S(S)34
Concise Formation of Spirocyclic Compounds for Marine Phycotoxins

Jun Ishihara,* Shingo Tojo, Takuya Makino, Hiroshi Sekiya, Akiko Tanabe, Mitsutaka Shiraishi, Akio Murai, and Susumi Hatakeyama*

*Graduate School of Biomedical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

The stereoselective construction of azaspiro[5.6]dodecenone skeletons by the chiral BOX/copper-mediated Diels-Alder reaction is described. The cycloaddition reaction of α-methylene caprolactams and functionalized dienes allows the concise formation of spirocyclic structures of marine phycotoxins, such as pinnatoxin and spirolide.