The Elsevier Tetrahedron natural Chemistry sequence is a topical sequence of monographs via world-renowned scientists in different fields of natural chemistry. The Tetrahedron natural Chemistry sequence has been very profitable in supplying many of the best possible scholarly works in those topical components that experience confirmed to be of lasting caliber as quintessential reference resources. those books have supplied the training researcher, scholar and pupil with a useful resource of accomplished studies in natural chemistry, predominantly within the components of synthesis and constitution decision, including:
* response mechanisms
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* Organometallic Chemistry
* Biologically very important Molecules
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Extra info for Advanced Problems in Organic Reaction Mechanisms
70. r with Rhodium(II) Acetate There has been great interest in recent years in methods for the generation of azomethine ylides and in exploitation of these reactive species in tandem/cascade processes for the rapid assembly of polyaza, polycyclic, multifunctional systems, tx-Diazo ketones have featured greatly in such studies, treatment with a catalytic amount of rhodium(II) acetate generating transient rhodium carbenoids. A very common feature of many investigations of this type is the occurrence of quite unexpected reactions.
25 A Furan to Pyran Ring Expansion The fungal metabolite wortmannin 1 shows a range of interesting and potentially useful biological properties. It has been reported, for example, to be a potent and selective inhibitor of phosphatidylinositol-3'-kinase, which has been identified as an important enzyme in a number of growth factor signalling pathways and is a potential target for intervention in certain proliferative diseases such as cancer. The C-21 position of wortmannin is highly electrophilic, and chemists at Eli Lilly and Company focused on this feature in attempts to modify the furan portion of 1, which was thought might be responsible for many of its biological activities.
For example, lithiation of 1,4-dioxene and addition of 2,2,6- trimethylcyclohexanone proceeded normally to give, after dehydration of the initially formed adduct, the expected diene A. Oxidation of A with MCPBA in methanol at 0oc gave B, C14H2404, in 70% yield as a mixture of diastereomers. Low temperature reaction of B with allyltrimethylsilane catalysed by EtA1C12 gave the protected o~-hydroxy ketone 1 in 85% yield. Outline the overall reaction scheme and suggest a mechanism for the conversion of B into 1.