Total synthesis of (-)-pironetin.
[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.
Dias
Luiz C
LC
Instituto de Química, Universidade Estadual de Campinas, UNICAMP, CP 6154 13083-970, Campinas, SP, Brazil. ldias@iqm.unicamp.br
De Oliveira
Luciana G
LG
De Sousa
Márcio A
MA
D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry
D011753:Pyrones; C088446:pironetin