STEREOSELECTIVE SYNTHESIS OF A CISOID C10ISOPRENOID BUILDING BLOCK AND SOME ALL-CIS-POLYPRENOLS

Abstract As the key compound for the construction of cisoid terpenoids, (2Z ,6Z)-8-benzyloxy-1-chloro-2,6-dimethylocta-2,6-diene was synthesized stereoselectively via the Wittig reaction starting from nerol. The ten-carbon building block was coupled with prenyl or neryl p-tolyl sulfone to afford, after reductive desulfonylation, (Z,Z)-farnesol and (Z,Z,Z) -nerylnerol, respectively.