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Catalytic Asymmetric Total Syntheses of (R)-Bgugaine and (R)-Irnidine

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DateAccepted/In press - 19 Nov 2020
DateE-pub ahead of print - 28 Nov 2020
DatePublished (current) - 8 Jan 2021
Issue number8
Number of pages9
Pages (from-to)1-9
Early online date28/11/20
Original languageEnglish


An enantioselective total synthesis of (R)-bgugaine and the first enantioselective total synthesis of (R)-irnidine are reported. The key steps are the asymmetric ‘clip-cycle’ formation of the pyrrolidine ring in 94:6 e.r., which is common to both natural products, followed by Liebeskind–Srogl coupling and Wolf-Kishner reduction. The route yields (R)-bgugaine and (R)-irnidine in 6 steps and in overall yields of 33% and 18% respectively.

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Invited submission to the Prof. Richard Taylor Special Issue

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