Theses and Dissertations
Issuing Body
Mississippi State University
Advisor
Mead, Keith T.
Committee Member
Hollis, T. Keith
Committee Member
Emerson, Joseph P.
Date of Degree
12-13-2014
Original embargo terms
MSU Only Indefinitely
Document Type
Graduate Thesis - Campus Access Only
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
Recommended Citation
Reyes, Yahaira De Bary, "Studies in Acceptor-Acceptor-Donor Cyclopropanes" (2014). Theses and Dissertations. 4117.
https://scholarsjunction.msstate.edu/td/4117
Comments
naphthol||acceptoreptor-donor cyclopropanes||Dragmacidin E