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Total synthesis of (-)-pironetin
Luiz C Dias1, Luciana G De Oliveira, Márcio A De Sousa
1Instituto de Química, Universidade Estadual de Campinas, UNICAMP, CP 6154 13083-970, Campinas, SP, Brazil. ldias@iqm.unicamp.br
Organic Letters
|January 31, 2003
Abstract:
[structure: see text] The asymmetric total synthesis of pironetin, a compound that shows plant growth regulatory activity, immunosuppressive as well as a remarkable antitumoral activity, is described. The approach involves the use of three very efficient Evans oxazolidinone-mediated syn-aldol condensations, a high-yielding coupling between lithium acetylide ethylenediamine complex and a tosylate followed by methylation, and selective reduction to establish the C12-C13 (E) double bond.