@unpublished{pittir39301,
           month = {September},
           title = {Synthetic Approaches to Cardiolipin Analogs},
          author = {Michael Frasso},
            year = {2020},
        keywords = {cardiolipin, organic synthesis},
             url = {http://d-scholarship-dev.library.pitt.edu/39301/},
        abstract = {The first portion of this document describes the synthesis of three examples of the mitochondrial phospholipid cardiolipin with different fatty acid chain lengths and degrees of unsaturation. These compounds enabled the assessment of the phospholipase Cld1?s hydrolysis specificity for different fatty acid esters in cardiolipin. 
During the final deprotection reaction of the synthesis, trace hydrolysis of the cardiolipin acyl groups occurred. To ameliorate this issue, a new protecting group scheme was devised, along with conditions for the selective cleavage of a primary triethylsilyl ether in the presence of a vicinal, secondary triethylsilyl ether, of which there are a surprisingly limited number of examples. 
Finally, a new method for cardiolipin synthesis was developed. The method was inspired by the biosynthetic remodeling of cardiolipin and allows for one of the fatty acids to be incorporated later in the synthetic, making it ideal for precious or sensitive fatty acids.}
}