Approaches directed toward synthesis of cephalostatin

Sang Who Lee, Purdue University

Abstract

The approaches directed toward the synthesis of Cephalostatin is described. The results of a model study involving $\gamma,\gamma$-dioxygenation of 2-methyl cyclohexenyl phenylsulfone by controlled endocyclic and exocyclic $\gamma$-metalation of $\beta$-substituted cyclohexenyl sulfones provides a regiospecific synthesis of $\gamma$-oxygenated cyclohexenyl sulfones. The synthetic studies which target construction of the D-ring of Cephalostatin are described. This project led to the development of a new strategy for palladium(0) -mediated intramolecular addition of sp$\sp2$ hybridized reagents to vinylsulfones. Subsequent metalation of the vinylsulfone provided a tricyclic ether via intramolecular alkylation of the sulfonyl-substituted allylic anion. The scope and limitations of this strategy are described. Finally, preparation of precursors for model studies related to the synthesis of benzene and pyridine analogs of Cephalostatin is described.

Degree

Ph.D.

Advisors

Fuchs, Purdue University.

Subject Area

Organic chemistry

COinS