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- W2105954795 abstract "Previous work at Salford involved the deprotonation of meso epoxide (Ha) withchiral lithium amide bases, to produce the crural allylic alcohol (Ilia) and theenantioselective deprotonation of meso ketone (I) to provide chiral silyl enol ether (V).In this thesis the potential utility of highly functionalised [3.3.0]bicyclooctane systems(Illb) and (VI) as flexible precursors to biologically active natural products isinvestigated.Meso epoxide (lib), was prepared stereoselectively in the exo form. Conditions wereexplored for transforming the epoxide to allylic alcohol (Illb), using a variety of chirallithium amide bases to provide optically active material. The e.e. of the product wasdetermined by conversion of the alcohol (Illb) to the corresponding benzoate ester andthen analysis by HPLC on chiral phase. The highest e.e. (54%) was achieved when (-)-sparteine^BuLi complex (IV) was used for deprotonation.In the first part of the thesis the construction of the linear triquinane skeletonwas investigated. Allylic alcohol (Illb) was converted to aldehyde (VII) via a 1,4-conjugate addition. Cyclisation of the third cyclopentane ring provided (IS*, 8R*)-cis-anti-cis-10,10-dimethyltricyclo[6.3.0.0]undec-3-one (VIII). This constitutes a formalsynthesis of the target triquinane hirsutene (IX).The triethylsilyl enol ether (V) was employed in the synthesis of the intermediate (VI).Several methods were attempted to generate intermediate (X) as a potential precursor toa range Corynanthe alkaloids via condensation with tryptamine.The ester (VI) was converted to the piperidone ring systems (Xlla) and (Xllb) bya Beckmann rearrangement of the corresponding tosylates (XI). The highlyfunctionalised piperidone (Xlla) has potential utility for the construction of a greatnumber of Corynanthe type monoterpenoid alkaloids.%3B&utm" @default.
- W2105954795 created "2016-06-24" @default.
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- W2105954795 date "1999-01-01" @default.
- W2105954795 modified "2023-09-24" @default.
- W2105954795 title "Enantioselective approaches to the synthesis of terpenoids and terpenoid derived alkaloids" @default.
- W2105954795 hasPublicationYear "1999" @default.
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