Synthetic studies towards furanocembrane diterpenes. A total synthesis of bis-deoxylophotoxin.
Synthetic approaches to the furanocembrane family of natural products, e.g. lophotoxins, pukalides, bipinnatins, based on: i) an intramolecular cyclisation of an alpha,beta-unsaturated acyl radical intermediate into a conjugated enone, and ii) an intramolecular Stille coupling reaction involving a 2-stannylfuran and a vinyl iodide, are described. A total synthesis of bis-deoxylophotoxin , the probable biological precursor to the neurotoxin lophotoxin, isolated from species of the Pacific sea whip Lophogorgia, is then presented.
Cases
Manuel
M
School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK.
Gonzalez-Lopez de Turiso
Felix
F
Hadjisoteriou
Maria S
MS
Pattenden
Gerald
G
D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D004224:Diterpenes; D005663:Furans; C511301:bis-deoxylophotoxin