Stereoselective synthesis of (Z)-5-(Trideca-4-enyl)resorcinol and gibbilimbols A-D

(Z)-5-(Trideca-4-enyl)resorcinol (1) and gibbilimbols A-D (2-5) were synthesized in 47%-60% yields over 6 steps from commercially available starting materials. The Wittig reaction of various alkyl phosphonium bromides with appropriate aldehydes in the presence of potassium tert-butoxide (t-BuOK) in anhydrous THF solution at room temperature served as the key step, and the result showed that only (Z)-configuration olefins were formed by this procedure. The synthesis of the (Z)-5-(trideca-4-enyl)resorcinol (1) was reported for the first time.