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Communication | Special issue | Vol 90, No. 2, 2015, pp.819-826
Published online, 6th August, 2014
DOI: 10.3987/COM-14-S(K)55
An Access to the 13-Membered Cyclophane Substructure in GKK1032As: An Intramolecular 1,4-Addition Approach

Satoka Nagai, Yuka Yamagishi, Yuta Shimizu, Ken-ichi Takao, and Kin-ichi Tadano*

*Department of Applied Chemistry, Emeritus, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, Japan


The construction of the 13-membered para-cyclophane substructure in GKK1032As, a member of novel pyrrolidinone-containing bioactive natural products, has been explored. An efficient approach for this synthetically formidable object was found, which relied on an intramolecular 1,4-addition between a nitromethylene group and a vinyl ketone moiety both incorporated as side chains into the 6/5/6-tricyclic (the A/B/C-ring system) of the GKK1032s.