The synthesis of trisporic acids Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/5425kd48x

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  • A total synthesis of the fungal hormones, trisporic acids A and B, is described, starting from a -methyltetronic acid 34. A Robinson annelation of 34 with ethyl vinyl ketone affords the lactone 33. Treatment of 33 with N-bromosuccinimide gave 97, which was hydrolyzed to the lactol 103. The reaction of 103 with diazomethane produced aldehyde 28. A Wittig reaction of 103 and the ylide 51 afforded (±)-(7E, 9E)- trisporic acid A in 16% yield. The phosphonium bromide 58 was prepared by a Wadsworth-Emmons condensation of 54 with valeraldehyde to give the trans adduct 55, which was reduced with lithium aluminum hydride to 56. Treatment of 56 with phosphorus tribromide gave 57, which was converted with triphenylphosphine to 58. A Wittig reaction of 103 and 29 furnished, after hydrolysis, (±)-(7E, 9E)-trisporic acid B (3). Treatment of 3 with diazomethane afforded a 5% yield of (±)-(7E, 9E)-trisporic acid B methyl ester, 12.
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