Normavacurine and Minfiensine, Two New Alkaloids with C19H22N2O Formula from Strychnos Species

Massiot, Georges; Thépenier, Philippe; Jacquier, Marie-José; Men‐Olivier, L. Le; Delaude, Clément

doi:10.3987/com-89-4987

Cited by 73 publications

(52 citation statements)

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“…5,6 In addition, HPIs which are fused with additional ring system such as a diketopiperazine moiety as in Brevicompanine B or polycyclic ring systems as in Minfiensine, Ardeemin or Okaramine N are known ( Figure 1). [7][8][9][10] These examples illustrate that the HPI core structure represents a biologically-validated scaffold and a library synthesis based on this scaffold should thus result in a compound collection with high biological relevance. [11][12][13] Due to the potent biological activities and the large structural diversity within this family, several approaches for their synthesis have evolved in the last decades.…”

Section: Introductionmentioning

confidence: 97%

Synthesis of a hexahydropyrrolo indole (HPI) compound library

Nickel

Hellmert

et al. 2015

Bioorganic & Medicinal Chemistry

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Section: Introductionmentioning

confidence: 97%

Synthesis of a hexahydropyrrolo indole (HPI) compound library

Nickel

Hellmert

et al. 2015

Bioorganic & Medicinal Chemistry

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“…Synthetic (+)-minfiensine (1) displayed 1 H and 13 C NMR spectral data identical to that reported for the natural product. 1 The optical rotation of synthetic (+)-minfiensine (1) …”

Section: Reductive Heck Cyclization To Form the Fifth Ring Completiomentioning

confidence: 99%

“…We envisaged minfiensine (1), as well as alkaloids of the vincorine family, to be accessible from 3,4-dihydro-9a,4a-(iminoethano)-9H-carbazole 7 (Scheme 1). The central transformation in our total synthesis plan is catalytic enantioselective formation of tetracyclic intermediate 7 from cyclohexadienyl carbamate 10.…”

Section: Synthesis Planmentioning

confidence: 99%

“…We also describe the details of our use of such an intermediate to complete the first total synthesis of minfiensine (1) 5 and our development of an improved end play that allows a notably efficient and concise catalytic asymmetric construction of this structurally unique Strychnos alkaloid to be realized.…”

Section: Introductionmentioning

confidence: 99%

“…1 Its structure was assigned using 1 H and 13 C NMR spectroscopy (C-H and H-H COSY, NOESY), with long-range coupling of the C15 methine hydrogen to the C17 allylic methylene and C19 vinylic hydrogens being particularly diagnostic. Although a variety of Strychnos alkaloids having a molecular formula of C 19 H 22 N 2 O have been isolated (e.g., 1-3 , Figure 1), the structure of minfiensine has no precedent.…”

Section: Introductionmentioning

confidence: 99%

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Total Synthesis of the Strychnos Alkaloid (+)-Minfiensine: Tandem Enantioselective Intramolecular Heck−Iminium Ion Cyclization

et al. 2008

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A 1,2,3,4-tetrahydro-9a,4a-(iminoethano)-9H-carbazole (4) is a central structural feature of the Strychnos alkaloid minfiensine (1) and akuammiline alkaloids such as vincorine (5) and echitamine (6). A cascade catalytic asymmetric Heck-iminium cyclization was developed that rapidly provides 3,4-dihydro-9a,4a-(iminoethano)-9H-carbazoles in high enantiomeric purity. Two sequences were developed for advancing 3,4-dihydro-9a,4a-(iminoethano)-9H-carbazole 27 to (+)-minfiensine. In our first-generation approach, a reductive Heck cyclization was employed to form the fifth ring of (+)-minfiensine. In a second more concise total synthesis, an intramolecular palladium-catalyzed ketone enolate vinyl iodide coupling was employed to construct the final ring of (+)-minfiensine. This second-generation total synthesis of enantiopure (+)-minfiensine was accomplished in 6.5% overall yield and 15 steps from 1,2-cyclohexanedione and anisidine 13. A distinctive feature of this sequence is the use of palladium-catalyzed reactions to form all carboncarbon bonds in the transformation of these simple precursors to (+)-minfiensine.

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Recent Advances on Stereoselective Organocatalytic Reactions. Organocatalytic Synthesis of Natural Products and Drugs

Raj

Singh

2011

Catalytic Methods in Asymmetric Synthesis

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Normavacurine and Minfiensine, Two New Alkaloids with C19H22N2O Formula from Strychnos Species

Cited by 73 publications

References 0 publications

Synthesis of a hexahydropyrrolo indole (HPI) compound library

Synthesis of a hexahydropyrrolo indole (HPI) compound library

Total Synthesis of the Strychnos Alkaloid (+)-Minfiensine: Tandem Enantioselective Intramolecular Heck−Iminium Ion Cyclization

Recent Advances on Stereoselective Organocatalytic Reactions. Organocatalytic Synthesis of Natural Products and Drugs

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