Convergent and Stereoselective Synthesis of Sarcophytol-Q Precursor: (11S)-3,7,11,15-Tetramethyl-11-hydroxy-14-oxo-3E,7E,12E-hexadecatrienal

A chiral precursor of sarcophytol-Q, (11S)-3,7,11,15-tetramethyl-11-hydroxy-14-oxo-3E,7E,12E-hexadecatrienal, was synthesized in a convergent and stereoselective manner starting from geraniol and 4-hydroxy-2-butanone in nine steps. The key steps were asymmetric Sharpless epoxidation, base-induced dehydrohalogenation rearrangement of chiral epoxy chloride 5 and the phase transfer catalytic coupling reaction of allylic phenyl sulfone 4 with chiral allylic chloride 3 .