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- W2803796021 abstract "Crinane embodies the tetracyclic framework associated with some of the most common Amaryllidaceae alkaloids. It has now been prepared in 10 steps from 6,6-dibromobicyclo[3.1.0]hexane (2). The initial step involves the thermally induced electrocyclic ring opening of cyclopropane 3 and capture of the resulting π-allyl cation with benzylamine to give an allylic amine that is readily elaborated to the 3°-amine 10. This last compound was engaged in a 5-exo-trig free radical cyclization reaction to give the C3a-arylated perhydroindole 11. Compound 11 was then converted, over two steps, into (±)-crinane, the hydrochloride salt of which has been subjected to single-crystal X-ray analysis." @default.
- W2803796021 created "2018-06-01" @default.
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- W2803796021 date "2018-05-24" @default.
- W2803796021 modified "2023-10-10" @default.
- W2803796021 title "Total Synthesis of (±)-Crinane from 6,6-Dibromobicyclo[3.1.0]hexane Using a 5-<i>exo</i>-<i>trig</i> Radical Cyclization Reaction to Assemble the C3a-Arylated Perhydroindole Substructure" @default.
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- W2803796021 doi "https://doi.org/10.1021/acs.joc.8b01088" @default.
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