Title

Studies in Acceptor-Acceptor-Donor Cyclopropanes

Advisor

Mead, Keith T.

Committee Member

Hollis, T. Keith

Committee Member

Emerson, Joseph P.

Date of Degree

1-1-2014

Original embargo terms

MSU Only Indefinitely

Document Type

Graduate Thesis - Open Access

Major

Chemistry

Degree Name

Master of Science

College

College of Arts and Sciences

Department

Department of Chemistry

Abstract

Isolated from Spongosorites sp., Dragmacidin E is of synthetic interest due to its biological properties and novel molecular structure. A promising therapeutic target, its synthetic challenge is attributed to its heptacyclic core. In this study, we propose the synthesis of a Dragmacidin E heptacyclic core precursor, mediated through a Lewis acid (LA) mediated cyclization of an acceptoreptor-donor (AAD) cyclopropane. Utilizing a model study, alkoxy AAD cyclopropanes were investigated to develop a protocol for precursor synthesis. After generating various ethyl-α-diazobenzoyl acetate derivatives, the metal catalyzed cyclopropanation reaction of these compounds was studied. With vinyl acetate and Rh2esp2, acetoxy AAD cyclopropanes were synthesized in yields ranging from 12 % - 53 %. These cyclopropanes were successfully generated and rearrangement into dihydrofuran products was avoided. To complete our model study, LA cyclization of acetoxy AAD cyclopropanes was studied. Using stoichiometric quantities of TiCl4<.sub>, naphthol derivatives were synthesized in one step.

URI

https://hdl.handle.net/11668/19048

Comments

naphthol||acceptoreptor-donor cyclopropanes||Dragmacidin E

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