Synthesis of the C(1)-C(18) segment of lophotoxin and pukalide. Control of 2-alkenylfuran (E/Z)-configuration.
[reaction: see text] The convergent synthesis of the fully functionalized C(1)-C(18) segment 24 of the furanocembranes lophotoxin and pukalide was accomplished in 11 steps and 10% overall yield. The key step was a stereoselective conversion of alkynoate 21 to trimethylsilyl 2-alkenylfuran 22.
Wipf
Peter
P
Department of Chemistry, University of Pittsburgh, Pennsylvania 15260, USA. pwipf+@pitt.edu
Soth
Michael J
MJ
D003064:Cnidarian Venoms / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D018733:Nicotinic Antagonists / Q000138:chemical synthesis* / Q000737:chemistry; D011978:Receptors, Nicotinic / Q000187:drug effects; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D003064:Cnidarian Venoms; D004852:Epoxy Compounds; D005663:Furans; D018733:Nicotinic Antagonists; D011978:Receptors, Nicotinic; D013729:Terpenes; C447623:pukalide; C030303:lophotoxin