Progress toward a biomimetic synthesis of phomoidride B.
[reaction: see text]. An intramolecular cyclization strategy for effecting a biomimetic synthesis of the core structure of the fungal secondary metabolites phomoidrides A and B is described. The cyclization substrate 20 is prepared in eight steps from dibromide 10. Treatment of 20 with triethylamine in acetonitrile results in a rapid cyclization to give 21 and 22 in good yield.
Sulikowski
Gary A
GA
Department of Chemistry, Texas A&M University, College Station, Texas 77842, USA. sulikowski@mail.chem.tamu.edu
Liu
Weidong
W
Agnelli
Fabio
F
Corbett
R Michael
RM
Luo
Zhushou
Z
Hershberger
Stefan J
SJ
D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008299:Maleic Anhydrides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D010407:Penicillium / Q000378:metabolism
C104957:CP 263114; D007202:Indicators and Reagents; D008299:Maleic Anhydrides