Studies toward the synthesis of cytochalasin C, and, Studies on the triggering mechanism in the activation of neocarzinostatin

Marie Lamothe, Purdue University

Abstract

The scope and limitations in the use of $\alpha$-stannyl, $\alpha$-silyl and $\alpha$-halo sulfones as latent $\alpha$-sulfonyl anions are described. Several initiators were studied for the intermolecular and intramolecular acylation of phenyl sulfones. A new ortho metalation/intramolecular trans-silylation of $\alpha$-silyl sulfones is presented. The chemistry of $\alpha$-hydroxy naphthoate esters is investigated to probe the eventual participation of the phenol naphthoate moiety in the triggering mechanism of neocarzinostatin activation and deactivation. It was found that they exhibit different types of intramolecular alkylation processes depending on the reaction conditions. Basic media show a mixture of C- and O-alkylation, whereas neutral and acidic manifolds exclusively produce compounds derived from ketene acetal formation.

Degree

Ph.D.

Advisors

Fuchs, Purdue University.

Subject Area

Organic chemistry

COinS