- The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids: A Modular “Inside-Out” Approach
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Bisquinolizidine alkaloids are characterized by a chiral bispidine core (3,7-diazabicyclo[3.3.1]nonane) to which combinations of an α,N-fused 2-pyridone, an endo- or exo-α,N-annulated piperidin(on)e, and an exo-allyl substituent are attached. We developed a modular “inside-out” approach that permits access to most members of this class. Its applicability was proven in the asymmetric synthesis of 21 natural bisquinolizidine alkaloids, among them more than ten first enantioselective total syntheses. Key steps are the first successful preparation of both enantiomers of C2-symmetric 2,6-dioxobispidine by desymmetrization of a 2,4,6,8-tetraoxo precursor, the construction of the α,N-fused 2-pyridone by using an enamine-bromoacrylic acid strategy, and the installation of endo- or, optionally, exo-annulated piperidin(on)es.
- Scharnagel, Dagmar,Goller, Jessica,Deibl, Nicklas,Milius, Wolfgang,Breuning, Matthias
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supporting information
p. 2432 - 2435
(2018/02/16)
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- A flexible strategy for the synthesis of tri- and tetracyclic lupin alkaloids: Synthesis of (+)-cytisine, (±)-anagyrine, and (±)-thermopsine
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(Chemical Equation Presented) Looping the lupin: A general synthetic strategy for the construction of the lupin alkaloids has been defined and involves sequential formation of the N1-C10 and C6-C7 bonds, which are common to compounds of this class of natu
- Gray, Diane,Gallagher, Timothy
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p. 2419 - 2423
(2007/10/03)
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