A new synthesis of gelsemine using a novel bridge-swapping strategy

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The synthesis of compact, densely functionalised, polycyclic natural products remains a challenge to synthetic chemists, and an important stimulus for the development of new synthetic methodology and strategies. The complex alkaloid target gelsemine is regarded as a classic challenge for organic synthesis, but despite attracting the attention of numerous research groups over the years only seven total syntheses have been accomplished, and these proceed by long (typically ca. 25 steps, with the shortest being around 18 steps) and largely inefficient routes. We plan to develop a new strategy (and some novel chemistry) that would enable a very short (maybe as few as 10 steps) new synthesis of this molecule. This would generate a new 'landmark' contribution to the area, as well as establishing more generally applicable synthetic chemistry.