ArticleThe Journal of organic chemistry2013
Enantioselective approach to quinolizidines: total synthesis of cermizine D and formal syntheses of senepodine G and cermizine C.
Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- A Catalytic, Enantioselective Sulfamate TetheredOrganic letters · 2024Article
- A safe and efficient synthesis of N-Boc-βRSC advances · 2024Article
- Synthesis of Demissidine Analogues from Tigogenin via Imine Intermediates.International journal of molecular sciences · 2021Article
- Transition metal catalyzed stereodivergent synthesis ofChemical science · 2019Article
- An expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks.RSC advances · 2018Article
- Enzymatic Kinetic Resolution of 2-Piperidineethanol for the Enantioselective Targeted and Diversity Oriented Synthesis.International journal of molecular sciences · 2015Review
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Authors and funding
5 authors.
Funding
Abstract
The formal syntheses of C5-epi-senepodine G and C5-epi-cermizine C have been accomplished through a novel diastereoselective, intramolecular amide Michael addition process. The total synthesis of cermizine D has been achieved through use of an organocatalyzed, heteroatom Michael addition to access a common intermediate. Additional key steps of this sequence include a matched, diastereoselective alkylation with an iodomethylphenyl sulfide and sulfone-aldehyde coupling/reductive desulfurization sequence to combine the major subunits. The utility of a Hartwig-style C-N coupling has been explored on functionally dense coupling partners. Diastereoselective conjugate additions to α,β-unsaturated sulfones have been investigated, which provided the key sulfone intermediate in just six steps from commercially available starting materials. The formal syntheses of senepodine G and cermizine C have been accomplished through an intramolecular cyclization process of a N-Boc-protected piperidine sulfone.
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Registered trials
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