SYNTHESES DE (R,S) MEVALONOLACTONES MARQUEES AU 14C OU AU 13C: (R,S) MEVALONOLACTONE (14C-4,5); (14C-5); (14C-3')

Article abstract of DOI:10.1016/S0040-4039(00)87294-9

Five new routes to (R,S) mevalonolactone suitable for the labelling with 14C or 13C at positions 4,5 or 5 or 3' are outlined.Three of them involve the use of the 2,4,10-trioxaadamantanyl group as a masked carboxyl.Two routes take advantage of the regioselective bis-hydroboration of a terminal alkyne.The acylation of the lithium carbanion of bis (trimethylsilyl) malonate and dithiane chemistry are also involved.The main feature is the use of isotope labelled acetylene and methyl iodide, both cheap isotopically labelled starting materials.