Cobalt Catalyzed Intramolecular Cyclization of Acyclic Alkenols for Polycyclic Ether Synthesis Pubblico

Abstract

Intramolecular cyclization reactions are useful to form fused cyclic ether rings like those observed in the natural product, brevenal. Stoichiometric amounts of mercury and iodide have been applied to acyclic alkenol substrates that resulted in brevenal’s ABC cyclic ether core with some limitations. We present a new metal catalyzed approach that will expand bis(1,3-diketonato)cobalt(II) intramolecular cyclizations beyond 5-membered tetrahydrofuran compounds. Studies with substituted alkenol substrates has provided suitable preliminary reaction conditions for product formation. Optimized reaction conditions will include the appropriate cobalt catalyst and efficient catalyst regeneration for successful product isolation.

Table of Contents

Introduction………………………………………………………………………………1

Results and Discussion…………………………………………………………………...5

Conclusion and Future Work…………………………………………………………….12

References………………………………………………………………………………..14

Experimental……………………………………………………………………………..18

About this Master's Thesis

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School	Laney Graduate School
Department	Chemistry
Degree	M.S.
Submission	Master's Thesis
Language	English
Research Field	Chemistry, Organic
Parola chiave	Co(II) complexes Alkenol Intramolecular cyclization Catalytic cyclization Stereoselective synthesis Tetrahydropyran Cyclic ether
Committee Chair / Thesis Advisor	McDonald, Frank E. , Emory University
Committee Members	Blakey, Simon, Emory University Davies, Huw, Emory University

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