Synthesis of cycloartenol via 19-oxygenated lanostanes
Abstract
U.v. irradiation of 3β-acetoxy-5α-lanost-24-en-11β-yl nitrite in the presence of oxygen affords 3β-acetoxy-11β-hydroxy-5α-lanost-24-en-19-yl nitrate. Further standard steps then give 3β-acetoxy-5α-lanosta-9(11),24-dien-19-yl methanesulphonate, which is reduced by lithium aluminium hydride in refluxing diethyl ether to afford cycloartenol in good overall yield.