ArticleOrganic letters2013
Enantioselective total synthesis of (+)-reserpine.
Article in Organic letters, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 61 citations in OpenAlex.
- Enantioselective Synthesis ofJACS Au · 2026Article
- Synthetic pathways to create asymmetric center at C1 position of 1-substituted-tetrahydro-β-carbolines - a review.RSC advances · 2024Review
- Enantioselective Syntheses of Yohimbine Alkaloids: Proving Grounds for New Catalytic Transformations.Synthesis · 2022Article
- A Concise, Enantioselective Approach for the Synthesis of Yohimbine Alkaloids.Journal of the American Chemical Society · 2020Article
- Development of bifunctional organocatalysts and application to asymmetric total synthesis of naucleofficine I and II.Nature communications · 2019Article
- Factors Controlling the Diels-Alder Reactivity of Hetero-1,3-Butadienes.ChemistryOpen · 2018Article
- Oxidative Asymmetric Formal Aza-Diels⁻Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones.Molecules (Basel, Switzerland) · 2018Article
- A Tryptoline Ring-Distortion Strategy Leads to Complex and Diverse Biologically Active Molecules from the Indole Alkaloid Yohimbine.Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
- A broadly applicable and practical oligomeric (salen) Co catalyst for enantioselective epoxide ring-opening reactions.Tetrahedron · 2014Article
- Divergent total syntheses of lyconadins A and C.Angewandte Chemie (International ed. in English) · 2014Article
- A practical method for the synthesis of highly enantioenriched trans-1,2-amino alcohols.Organic letters · 2013Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
A catalytic, enantioselective synthesis of (+)-reserpine is reported. The route features a highly diastereoselective, chiral catalyst-controlled formal aza-Diels-Alder reaction between a 6-methoxytryptamine-derived dihydro-β-carboline and an enantioenriched α-substituted enone to form a key tetracyclic intermediate. This approach addresses the challenge of setting the C3 stereogenic center by using catalyst control. Elaboration of the tetracycle to (+)-reserpine includes an intramolecular aldol cyclization and a highly diastereoselective hydrogenation of a sterically hindered enoate.
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