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The synthesis of functionalized heteroaromatic compounds is of high importance in the discovery of novel herbicides. In this Letter is reported the synthesis of a series of 2-heteroaromatic-1,3-diones utilizing a Claisen rearrangement to form a key carbon–carbon bond. The paper focuses on the scope and diversity of the molecules synthesized via this route.
The synthesis of (3S,5S)-quinuclidine-3,5-diol is achieved by an introduction of a 2 carbon chain at C-3 of D-arabinose, followed by joining the terminus of the chain extension to C-1 and C-5 of the sugar; the synthesis of [3S-(3α,3aα,7aα)]-octahydro-2-furo[2,3-c]pyridinol, a potential muscarine mimic, is described.
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