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Short Paper | Special issue | Vol 84, No. 2, 2012, pp.1301-1304
Published online, 21st July, 2011
DOI: 10.3987/COM-11-S(P)51
Practical Total Synthesis of Luotonin A by Intramolecular Double Hetero Diels-Alder Reaction

Ken Natsuki, Tadamichi Shindo, and Masahiro Toyota*

*Department of Chemistry, Graduate School of Science, Osaka Prefecture University, 1-1 Gakuencho, Sakai, Osaka 593-8531, Japan


An intramolecular double hetero Diels–Alder reaction of N-(2-cyanoquinolin-3-ylmethyl)-2-tosyloxybenzamide (3c) provided luotonin A (2) in 82% yield. Surprisingly, N-(2-bromoquinolin-3-ylmethyl)-2-tosyloxybenzamide (4) directly provided luotonin A (2) in 78% yield in the presence of Pd2(dba)3 (5 mol %), dppf (20 mol %), and K2CO3 (6 eq).