The Synthesis of the Macrolide Antibiotic (+/-)-Pyrenophorin

Purcell, Thomas Andrew (1973) The Synthesis of the Macrolide Antibiotic (+/-)-Pyrenophorin. PhD thesis, University of Glasgow.

Abstract

The synthesis of the macrolide antibiotic (+/-)-pyrenophorin (1) is described. The molecular sieve promoted cyclisation of the hydroxy methyl ester (135) failed in our hands but the hydroxy-acid (190) was successfully converted to the dithioacetal of (1) using N,N'-carbonyldiimidazole (207) and 1,5-diazabicyclo(4,3,0)-non-5-ene (147). A novel method of removing p-toluenesulphonylethyl esters (166) is reported as is a new simple technique of hydroxyl alkyl-ation involving molecular sieves and sodium hydrogen carbonate.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry, Pharmacology
• Date of Award: 1973
• Depositing User: Enlighten Team
• Unique ID: glathesis:1973-78636
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 30 Jan 2020 15:07
• Last Modified: 30 Jan 2020 15:07
• URI: https://theses.gla.ac.uk/id/eprint/78636