Development and Optimization of Monosubstituted and Disubstituted Alkene Synthesis for Future Intramolecular Alkene Hydroalkoxylation Reactions Public

Abstract

Chapter 1:  Brevenal, Brevetoxin, and other marine ladder-frame polyether natural products

Brevenal, a fused polycyclic ether produced by the same dinoflagellate Karenia brevis, acts as an antagonist to brevetoxin reducing the effects of neurotoxic shellfish poisoning and making it a potential treatment option for organisms exposed to brevotoxin and other mucociliary diseases such as cystic fibrosis. Our research will explore the formation of six- and seven-membered ethers through an intramolecular alkenyldiol cyclization for future one-step cyclization cascade of the polycyclic ether structure in fused polycyclic ether natural products.

Chapter 2: Substrate synthesis for intramolecular cyclization reactions of alkenyldiols 

This chapter focuses on the development of substrates (i.e monosubstituted alkenes and disubstituted alkenes) for intramolecular cyclization reactions. This chapter explores the synthetic route for substrates for future one-step cyclization reactions with various catalysts. Furthermore, this chapter explores future direction for cyclization reactions.

Table of Contents

Chapter 1:  Brevenal, Brevetoxin, and other marine ladder-frame polyether natural products

1.1  Background....................................................................................................................1

1.2  Utility of Monosubstituted and Disubstituted Alkenes...................................................4

1.3  Background on Intramolecular Hydroalkoxylation.......................................................4

1.4  Preparation of Oxacyclization Reactions of Alkenyl alcohols......................................6

1.4.1  Mercury Cyclization

1.4.2  Iodocyclization

1.5  Focus on One Step Cyclization of Oxacyclization Reactions of Alkenyl diols................8

Chapter 2: Substrate synthesis of intramolecular cyclization reactions of alkenyldiols  

2.1 Design of Precursors for Cyclization Reactions.........................................................10

2.1.1 Monosubstituted Alkenes

2.1.1.1 Early Oxidation Results

 2.1.1.2 Discovery with Vinylmagnesium Bromide

2.1.2 Disubstituted Alkene

2.2 Synthetic Pathway for Disubstituted Cis-Alkene...........................................................13

2.2.1 Mechanism of Ni(OAc)2 and NaBH4 Hydrogenation 

2.2.2 Challenges with Ni(OAc)2, NaBH4, and H2 Gas for Stereoselective Hydrogenation 

2.3 Problems with Deprotection of TBDMS.....................................................................15

2.4 Future Direction.........................................................................................................15

2.5 Experimental Results 

About this Honors Thesis

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School	Emory College
Department	Chemistry
Degree	B.A.
Submission	Honors Thesis
Language	English
Research Field	Chemistry, Organic
Mot-clé	Brevenal
Committee Chair / Thesis Advisor	Dr. Frank McDonald, Emory University
Committee Members	Dr. Keith Berland, Emory University Dr. Brian Dyer, Emory University

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