A ring fragmentation and intramolecular azomethine ylide 1,3-dipolar cycloaddition sequence of reactions was successfully used in the preparation of a known (+/-)-cycloclavine precursor in good overall yield. Results of efforts to incorporate the tetrasubstituted cyclopropane ring present in cycloclavine are also discussed. (C) 2013 Elsevier Ltd. All rights reserved.
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Waseda Univ, Dept Chem & Biochem, Fac Sci & Engn, Shinjuku Ku, Tokyo 1698555, JapanWaseda Univ, Dept Chem & Biochem, Fac Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan
Asakawa, Kaori
Noguchi, Naoyoshi
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Waseda Univ, Dept Chem & Biochem, Fac Sci & Engn, Shinjuku Ku, Tokyo 1698555, JapanWaseda Univ, Dept Chem & Biochem, Fac Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan
Noguchi, Naoyoshi
Nakada, Masahisa
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Waseda Univ, Dept Chem & Biochem, Fac Sci & Engn, Shinjuku Ku, Tokyo 1698555, JapanWaseda Univ, Dept Chem & Biochem, Fac Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan