Towards the Synthesis of Marine Polyether Triterpenes Pubblico

Abstract

The carbon skeleton of marine polyether triterpenes: thyrsiferol, dehydrothyrsiferol, thyrsenols A and B has been constructed. Carbon-carbon bonds were successfully created by nucleophilic opening of terminal epoxides and palladium catalyzed cross coupling. Oxygen containing stereocenters were set by asymmetric epoxide formation and asymmetric dihydroxylation. Cyclic ethers were formed by acid catalyzed hydroxyepoxide oxacyclizations, tungsten promoted alkynol endocyclization, and the Nakata rearrangement.

Table of Contents

1.0) Introduction 1 2.0) Previous Synthesis of the ABC Tristetrahydropyran Ring System 3 2.1) Revised Synthesis of B Ring 5 2.2) Attempted Carbon-Carbon Bond Construction via Sulfur Mediated Anions 8 2.3) Revised Retrosynthetic Strategy 10 2.4) Construction of C Ring 12 2.5) Assembly of the D Ring 14 2.6) Stille Cross Coupling 15 2.7) Efforts to Functionalize Unsaturated Centers 16 3.0) Conclusion 18 Experimental 19 References 40

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School	Laney Graduate School
Department	Chemistry
Degree	MS
Submission	Dissertation
Language	English
Research Field	Chemistry, Organic
Parola chiave	Dehydrothyrsiferol Thyrsiferol Thyrsenols A and B Venustatriol polyether terpenoids epoxidation tungsten promoted alkynol endocyclization
Committee Chair / Thesis Advisor	McDonald, Frank, Emory University
Committee Members	Liotta, Dennis C, Emory University Liebeskind, Lanny S, Emory University

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