Approaches to the synthesis of macrocyclic ketones and approaches to the total synthesis of the pseudonomic acids and trinervitane

Higgs, Laurie Stewart (1988) Approaches to the synthesis of macrocyclic ketones and approaches to the total synthesis of the pseudonomic acids and trinervitane. University of Southampton, Doctoral Thesis.

Abstract

Chapter one describes an approach to the synthesis of macrocyclic ketones via the Claisen rearrancement of cyclic allyl vinyl ethers. A model study involving the use of a pendant vinyl group was successful but attempts to substitute this group for a cycloalkene and perform the rearrangement were unsuccessful. Chapter two describes approaches to the tricyclic diterpene trinervitane, a defence secretion isolated from soldier termites. These approaches were based upon a protected bicyclo [4,3,0] nonandione produced by Robinson annelation of a five membered-ring ketone. Attempts to produce the cycloundecane ring and reactivities of the bicyclo [4,3,0] nonandiones are reported. Chapter three describes the attempted total synthesis of pseudomonic acid, an antibiotic isolated from pseudomonas fluorenscens. Initial syntheses were based upon the production of the unknown α-pyran and subsequent Diels-Alder chemistry. Later methods started from the 2π+ 2π reaction of dihydropyran with various ketenes.

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