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A biomimetic approach to the synthesis of sarcoglane

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Description: Sarcoglane, a cytotoxic diterpene produced by the soft coral Sarcophyton glaucum possesses a unique tricyclo[7,5,0 10,14 ]tetradecenone ring system. Biosynthetic analysis implies that the tricycle is derived via a cationic cascade from geranylgeranyl diphosphate, yielding a cembrane. The goal of this research is to synthesize an analog of this cembrane, then induce polycyclization to produce sarcoglane. The cembrane is synthesized via additive reactions on a silylated butenoic acid, produced by an irregular Grignard reaction on diketene. This primary constituent becomes a silylated analog of geranial after the appropriate modifications. These modifications represent the bulk of the research, as multiple alkylation approaches were explored. Allylation will be used to construct a geranylgeranyl analog in a convergent fashion and Stille coupling will be used to form the macrocyclic cembrane precursor. A chloride leaving group on the cembrane, representing a masked carbocation, will prepare the molecule for the silver-induced ring closure en route to sarcoglane.
Language: English
Format: Degree Work