Synthesis of (+)-spirolaxine methyl ether.
A short and efficient synthesis of (+)-spirolaxine methyl ether, a metabolite of the fungus Sporotrichum laxum with inhibitory activity against Helicobacter pylori, is described. The synthesis has been carried out by a Prins cyclization, to obtain the [6,5]-spiroketal system, and a Wadsworth-Emmons condensation, applied for the installation of the polymethylene chain on the phthalide moiety.
Nannei
Raffaella
R
Dipartimento di Scienze Molecolari Agroalimentari, Università di Milano, Via Celoria 2, 20133 Milano, Italy.
Dallavalle
Sabrina
S
Merlini
Lucio
L
Bava
Adriana
A
Nasini
Gianluca
G
D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D013141:Spiro Compounds; C517924:spirolaxine methyl ether