Synthesis of the naturally occurring cyclopropenoids malvalic and sterculic acids

Graduation date: 1966The two naturally occurring cyclopropene fatty acids, sterculic\ud and malvalic, have been synthesized. The cyclopropene ring was\ud made by inserting a methylene unit into an acetylenic linkage.\ud The synthesis of methyl sterculate was repeated using diethyl\ud aluminum chloride, diazomethane, and methyl stearolate.\ud Methyl malvalate was totally synthesized. Diethyl malonate\ud was condensed with 1, 5-dibromopentane to give 7-bromoheptanoic\ud acid. 1-Decyne was reacted with 7-bromoheptanoic acid to give\ud 7-heptadecynoic acid. 7-Heptadecynoic acid was esterified with\ud diazomethane. The cyclopropene ring was generated using diethyl\ud aluminum chloride and diazomethane.\ud The reaction worked very well and in most cases the yields\ud exceeded 50 percent