Construction of the ACDE Ring System of Calyciphylline A-type Alkaloids via Intramolecular Diels-Alder Reaction of a Tetrasubstituted Olefin

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A concise synthesis of the ACDE tetracyclic ring system of calyciphylline A-type alkaloids was investigated. The intramolecular Diels–Alder reaction of a tetrasubstituted olefin with furan enabled the construction of the ACD ring system bearing two contiguous quaternary carbons in one step, and subsequent intramolecular [3+2] cycloaddition successfully gave the E ring.

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  • Synlett

    Synlett 30 2253-2257, 2019-01-01

    Georg Thieme Verlag

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