A new group of juvenoids with the 5,5‐dimethylcyclohex‐3‐ene system was obtained by a multi‐step synthesis starting from (+)‐3‐carene (1). Esters 15, 16 and 18 were synthesized by the Wadsworth‐Emmons reaction of ketone 14 or aldehyde 17 with appropriate phosphonates. Esters 19 and 20 were obtained by the Claisen rearrangement of allylic alcohol 21 with trimethyl or triethyl orthoacetate. Juvenoids obtained were active against Dysdercus cingulatus and were inactive against Tenebrio molitor.
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Wawrzeńczyk et al. (1988) studied this question.
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