Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (−)-lupinine, and (+)-epiepiquinamide

Fustero, Santos; Moscardó, Javier Ruiz; Sánchez‐Roselló, María; Flores, Sonia; Guerola, Marta; Pozo, Carlos del

doi:10.1016/j.tet.2011.07.017

Cited by 36 publications

(22 citation statements)

References 51 publications

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“…[10] In 2011, the authors were able to extend their protocol to the synthesis of quinolizidine alkaloids (+)-myrtine 21, (À)-lupinine 23, and (+)-epiepiquinamide 24 (Scheme 5). [11] Similar to the previous procedures, Mi- chael adduct 20 with 63 % yield and 94 % ee was obtained using diarylprolinol silylether 3 together with benzoic acid as a catalytic system.…”

Section: Intramolecular Aza-michael Additionsmentioning

confidence: 64%

Advances and Applications in Organocatalytic Asymmetric aza‐Michael Addition

et al. 2012

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Section: Intramolecular Aza-michael Additionsmentioning

confidence: 64%

Advances and Applications in Organocatalytic Asymmetric aza‐Michael Addition

et al. 2012

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“…Moreover, the Fustero group [48] accomplished the enantioselective total syntheses of other three quinolizidine alkaloids, namely, (+)-myrtine, (−)-lupinine, and (+)- epi epiquinamide via the same asymmetric aza -Michael reaction (Scheme 15).…”

Section: Asymmetric Total Synthesis Of Bioactive Natural Products mentioning

confidence: 99%

Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes

Wang

2019

Molecules

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Chirality is one of the most important attributes for its presence in a vast majority of bioactive natural products and pharmaceuticals. Asymmetric organocatalysis methods have emerged as a powerful methodology for the construction of highly enantioenriched structural skeletons of the target molecules. Due to their extensive application of organocatalysis in the total synthesis of bioactive molecules and some of them have been used in the industrial synthesis of drugs have attracted increasing interests from chemists. Among the chiral organocatalysts, chiral secondary amines (MacMillan’s catalyst and Jorgensen’s catalyst) have been especially considered attractive strategies because of their impressive efficiency. Herein, we outline advances in the asymmetric total synthesis of natural products and relevant drugs by using the strategy of chiral secondary amine catalyzed reactions of α,β-unsaturated aldehydes in the last eighteen years.

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“…21 Fustero and co-workers utilized their intramolecular organocatalyzed aza-Michael addition reaction 22 for the enantioselective total synthesis of myrtine (51) (Scheme 6). 23 The aza-Michael reaction was used to obtain the piperidine ring 50 in high enantioselectivity (94% ee) from the enal precursor 48. The aldehyde 50 was converted into myrtine (51) in the succeeding steps.…”

Section: Development Of the Heteroatom Michael Reactionmentioning

confidence: 99%

Lycopodium Alkaloids: An Intramolecular Michael Reaction Approach

Saha¹,

Carter²

2017

Synlett

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The Lycopodium alkaloids possess a rich history that has captured the attention of synthetic chemists across the globe. This large family consists of over 250 known natural products with diverse structural features and noteworthy biological activity. Herein, we interweave the synthetic accomplishments by others in the field with our own unified strategy to accessing multiple subfamilies of the Lycopodium alkaloids. This discussion includes lycopodine, the C10-hydroxy Lycopodium alkaloids (10-hydroxylycopodine, deacetylpaniculine and paniculine), pelletierine, cermizine D, fastigiatine, himeradine A, clavolonine and 7-hydroxylycopodine. A unifying feature of much of the work discussed within this account is the use of intramolecular Michael additions to construct key ring systems within the Lycopodium alkaloids. Examples include the use of an intramolecular keto-sulfone Michael reaction and an intramolecular heteroatom Michael reaction.1 General Background on Lycopodium Alkaloids2 Development of a Strategy for Lycopodium Alkaloids2.1 Generalized Strategy2.2 Known Syntheses of C10-Functionalized Lycopodium Alkaloids3 Quinolizidine-Type Alkaloids3.1 Background3.2 Development of the Heteroatom Michael Reaction3.3 Synthesis of the Core Lycopodine Building Block: Pelletierine3.4 Total Synthesis of Cermizine D3.5 Synthesis of the Eastern Half of Himeradine A4 Lycopodine-Type Alkaloids4.1 Total Syntheses of Lycopodine4.1.1 Earlier Racemic Syntheses4.1.2 Approach Toward the Tricyclic Skeleton of Lycopodine: Intramolecular Mannich4.1.3 Enantioselective Total Syntheses of Lycopodine4.2 Total Syntheses of Clavolonine (8-Hydroxylycopodine)4.3 Total Synthesis of 7-Hydroxylycopodine4.4 Synthetic Route for 10-Hydroxy Lycopodium Alkaloids4.4.1 Background4.4.2 Total Syntheses4.4.3 Impact of the C10-Stereochemistry5 Conclusion

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Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (−)-lupinine, and (+)-epiepiquinamide

Cited by 36 publications

References 51 publications

Advances and Applications in Organocatalytic Asymmetric aza‐Michael Addition

Advances and Applications in Organocatalytic Asymmetric aza‐Michael Addition

Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes

Lycopodium Alkaloids: An Intramolecular Michael Reaction Approach

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