Partial Synthesis of Novel Trichothecene Mycotoxins

Organic chemistry, Biochemistry

Thomas, Gerard Hugh

University:University of Glasgow

关键词: Organic chemistry, Biochemistry;   

Others  :  http://theses.gla.ac.uk/75842/1/13818578.pdf

来源: University of Glasgow

【 摘 要 】

The partial syntheses of two novel trichotheoene homologues, (13R)-3alpha,4beta, 15-triacetoxy-13-methyl-12,13-epoxy trichothec-9-ene (11) and (13S)-3alpha,4beta-triacetoxy-13-methyl-12,13-epoxytrichothec-9-ene (12), from the readily available trichothecenes DAS (1) (4beta,15-diacetoxy-3alpha-hydroxy-12,13-epoxytrichothec-9-ene) and MAS (2) (3alpha,15-dihydroxy-4beta-acetoxy-12,13-epoxytrichothec-9-ene) are detailed. These were carried out in order to provide further insight into the mode of action of the trichothecene mycotoxins. In addition, a model study was conducted which involved the synthesis of the bicyclo[3.2.1]octane epoxy alcohol (96) and the bicyclo[3.2.1]octane epoxy triethylsilyl ethers (110) and (111) from 2-methyl cyclohexanone.