Angewandte Chemie International Edition
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Communication
Total Synthesis of (−)-Melotenine A†
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Financial support from the NSF (CHE-1111558) is gratefully acknowledged. We thank Dr. Charles DeBrosse, Director of the NMR Facilities at Temple Chemistry, for kind assistance with NMR experiments. We thank Prof. Chris Schafmeister (Temple University) for access to LC-MS instrumentation. Finally, we thank Dr. Richard Pederson (Materia, Inc.) for catalyst support.
Abstract
'Melo' out: A concise asymmetric synthesis of (−)-melotenine A has been accomplished in fourteen steps and 1 % overall yield from commercial N-tosylindole-3-carboxaldehyde. Key steps include a Piers annulation, an intermolecular vinylogous aldol reaction, and a novel one-pot sequence to prepare the ABCE tetracycle. Boc=tert-butoxycarbonyl, Ts=4-toluenesulfonyl.