A STEREOSELECTIVE FORMATION OF (Z)-2-METHYL-2-ALKENOL BY THE WITTIG REACTION: ITS APPLICATION TO A SYNTHESIS OF NERYLACTONE AND (Z,Z)-FARNESYLACTONE
The Wittig reaction of benzyloxyacetone or tetrahydropyranyloxyacetone with 4-pentynylidenetriphenylphosphorane in salt-free conditions followed by removal of the protecting group afforded (Z)-2-methylhept-2-en-6-yn-1-ol in 95-96percent stereoselectivity.