Studies towards the total synthesis of dictyoxetane

Sembayeva, Aliya (2017). Studies towards the total synthesis of dictyoxetane. University of Birmingham. M.Sc.

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Abstract

Dictyoxetane, a structurally unique diterpene from the dollabelane family of natural products, was isolated from the brown algae, \(Dictyota\) \(dichotoma\), from the Indian Ocean in 1985. The structure of dictyoxetane was later elucidated by X-ray crystallographic analysis, but it is only recently that the absolute stereochemistry became known. Its unique tricyclic core, containing both tetrahydrofuran and oxetane moieties, makes it a synthetic challenge.

Chapter 1 reviews the history of dictyoxetane and previous synthetic work towards the synthesis of its dioxatricyclic ring system. Previous work in the Grainger group on the asymmetric approach towards the key intermediate, \(trans\)-hydrindane is described, along with various synthetic approaches to [3.2.1] oxabicyclic ring systems. Furthermore, updated methodologies are described outlining the synthesis of [3.2.1] oxabicyclic systems.

Chapter 2 covers the current asymmetric synthesis of the \(trans\)-hydrindane intermediate starting from the Hajos-Parrish ketone. In addition, TBAF-mediated 5-\(exo\)-\(dig\) cyclization to a tetrasubstituted furan system followed by [4+3] cycloaddition with an oxyallyl cation under Hoffmann’s conditions leading to the formation of other novel oxabicyclic systems is described.

Type of Work:

Thesis (Masters by Research > M.Sc.)

Award Type:

Masters by Research > M.Sc.

Supervisor(s):