The Synthesis of Lauraceae Lactones: Obtusilactones, Litsenolides, and Mahubanolides

Phenylselenenyl esters (methyl esters of 2-phenylselenenylhexadecanoic, 2-phenylselenenyloctadecanoic, and 2-phenylselenenyl-13-tetradecadienoic acids) were used as acrylate (alpha)-anion synthons in aldol addition reactions. The last acid above, bearing the terminal double bond, was synthesized by displacing the (omega)-bromide from methyl 11-bromo-2-phenylselenenylundecanoate by allyllithium. The other (alpha)-phenylselenenyl esters were made by quenching their lithium enolates with phenylselenenyl chloride. Addition to acrolein, followed by oxidation and selenoxide elimination gave the corresponding (alpha),(beta)-unsaturated esters bearing a 1-hydroxy-2-propenyl group at the (alpha)-carbon. Similarly, addition to propargylaldehyde followed by oxidative work-up gave the corresponding (alpha),(beta)-unsaturated esters bearing a 1-hydroxy-2-propynyl group at the (alpha)-carbon.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2014

Author dc:creator

• Rollinson, Susan Lynn Wells

• Chemistry, Organic

Language dc:language

eng

Identifier

(UMI)AAI8108644

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/67250