Catalytic crossed Michael cycloisomerization of thioenoates: total synthesis of (+/-)-ricciocarpin A.
[reaction: see text] Thioenoates are found to participate in highly chemoselective catalytic crossed Michael cycloisomerization with appendant aryl ketone and enoate partners to afford cyclopentene and cyclohexene products. This methodology has enabled a concise total synthesis of the potent molluscicide (+/-)-ricciocarpin A.
Agapiou
Kyriacos
K
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
Krische
Michael J
MJ
D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D007536:Isomerism; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D008975:Molluscacides / Q000138:chemical synthesis*; D010944:Plants / Q000737:chemistry
D005663:Furans; D007659:Ketones; D008975:Molluscacides; C476521:ricciocarpin A