I The synthesis of papyracillic acids: Application of the tandem chain extension-acylation reaction II Diastereoselective synthesis of beta-methyl-gamma-keto esters through the utility of an L-serine auxiliary

<p>The development of the zinc-mediated tandem chain extension-acylation reaction for the synthesis of spiro-fused ketals was successfully accomplished. The incorporation of a methyl-substituent into the gamma-keto ester backbone, through a methyl substituted carbenoid, allowed for the synthesis of papyracillic acid B and 4-epi-papyracillic acid C. Comparison between the reported and experimental spectral data for papyracillic acid B and 4- epi-papyracillic acid C permitted structural and stereochemical reassignment.</p><p>Diastereoselective syntheses of beta-methyl-gamma-keto esters were achieved through the utility of an L-serine auxiliary. Preparation of a series of L-serine derived precursors were prepared and studied.</p>

Name thesis:degree_name

Doctor of Philosophy

Level thesis:degree_level

Dissertation

Year

2011

Author dc:creator

• Mazzone, Jennifer R

Contributors dc:contributor

• Charles K Zercher

• Chemistry
• Organic

Repository record dc:identifier

https://scholars.unh.edu/dissertation/644

OAI identifier oai:identifier

oai:scholars.unh.edu:dissertation-1643