Abstract

Soft sea corals generate a plethora of natural products including steroids and metabolites. As such, they have been of keen interest to biologists and synthetic organic chemists. Recently the soft corals Sarcophyton trocheliophorum and Lithophyton arboretum, which were isolated from the Gulf of Aqaba in the Red Sea, have been found to produce six butenolide lipids and butenolides with unusual substitution and unsaturation patterns. The purpose of this research is to achieve the total synthesis of the gamma-lactone 1, Trocheliophorolide A, one of the six butenolide natural products. Trocheliophorolide A is composed of a lactone ring and a unique unsaturated side chain. This thesis will describe the previous successful synthesis of the lactone ring portion of Trocheliophorolide A, followed by the previously explored routes for synthesizing the unsaturated side chain that were not successful. This thesis specifically discusses the successful synthesis of the acid chloride side chain in a five-step, efficient route with satisfactory overall yields. Additionally, both model study cross-coupling reactions and the actual final cross-coupling reaction are explored and discussed.

Library of Congress Subject Headings

Lactones--Synthesis; Ketones--Synthesis; Organic compounds--Synthesis; Antibacterial agents

Publication Date

2013

Document Type

Thesis

Student Type

Graduate

Degree Name

Chemistry (MS)

Department, Program, or Center

School of Chemistry and Materials Science (COS)

Advisor

Christina Goudreau Collison, Ph. D.

Advisor/Committee Member

Paul Craig, Ph. D.

Advisor/Committee Member

Michael G. Coleman

Comments

Note: imported from RIT’s Digital Media Library running on DSpace to RIT Scholar Works in July 2014. Physical copy available from RIT's Wallace Library at QD305.A2 S93 2013

Campus

RIT – Main Campus

Plan Codes

CHEM-MS

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