The chemistry of mavacurane alkaloids: a rich source of bis-indole alkaloids

Mauger, Audrey; Jarret, Maxime; Kouklovsky, Cyrille; Poupon, Erwan; Evanno, Laurent; Vincent, Guillaume

doi:10.1039/d0np00088d

Cited by 20 publications

(35 citation statements)

References 152 publications

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“…The choice of the last ring and bond to form is key to the success of such endeavor (Scheme 1). 1 For instance, inspired by the postulated biosynthesis of the mavacurans, 1,6 final formations of the N1-C16 bond and the E ring have been targeted for several decades from tetracyclic ABCD derivatives (geissoschizine-type). 1 In 1972, Boekelheide was able to form the pseudoindoxyl skeleton of unnatural 19-20-dihydro-norfluorocorine via the opening of a C16-epoxide by the N1 indolic nitrogen.…”

Section: Figure 1 Mavacuran Alkaloidsmentioning

confidence: 99%

“…1 For instance, inspired by the postulated biosynthesis of the mavacurans, 1,6 final formations of the N1-C16 bond and the E ring have been targeted for several decades from tetracyclic ABCD derivatives (geissoschizine-type). 1 In 1972, Boekelheide was able to form the pseudoindoxyl skeleton of unnatural 19-20-dihydro-norfluorocorine via the opening of a C16-epoxide by the N1 indolic nitrogen. Subsequently, reduction of the carbonyl and acid-mediated expansion of the C ring via a 1,2-shift of the C6-carbon from the C2 to the C7 positions led to unnatural 19-20-dihydronormavacurine.…”

Section: Figure 1 Mavacuran Alkaloidsmentioning

confidence: 99%

“…2 The pentacyclic mavacuran skeleton is characterized by a C-N bond between the N1 indole nitrogen and the C16 carbon of the geissoschizine framework (Figure 1). 1 Cmavacurine (1) and pleiocarpamine (2) are the two representative members of this family. 1,3 C-mavacurine (1) 3a-d is the name-giver of this sub-family and pleiocarpamine (2) 3a,e,f is a constitutive unit of several complex indole alkaloids including bis-indole alkaloids.…”

Section: Introductionmentioning

confidence: 99%

“…1 Cmavacurine (1) and pleiocarpamine (2) are the two representative members of this family. 1,3 C-mavacurine (1) 3a-d is the name-giver of this sub-family and pleiocarpamine (2) 3a,e,f is a constitutive unit of several complex indole alkaloids including bis-indole alkaloids. 1…”

Section: Introductionmentioning

confidence: 99%

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Collective Total Synthesis of Mavacuran Alkaloids via an Intermo-lecular 1,4-Addition Approach

Mauger

Jarret

Tap

et al. 2022

Preprint

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We report a synthetic endeavor towards the highly strained pentacyclic caged framework of the mavacuran alkaloids which culminated with the concise total synthesis of C-fluorocurine, C-profluorocurine, C-mavacurine, normavacurine, 16-epi-pleiocarpamine and taberdivarine H. We designed an original strategy which involves a late stage construction of the D ring via a Michael addition of a vinylic nucleophile to a 2-indolyl acrylate moiety. While the intramolecular Michael addition did not succeed, we were able to perform a diastereoselective unusual intermolecular 1,4-addition of a functionalized vinyl lithium reagent onto a readily accessible Michael acceptor. Final cyclization was achieved via nucleophilic substitution into an ammo-nium intermediate. The first total syntheses of C-profluorocurine and C-fluorocurine were finalized via respectively the dihy-droxylation of C-mavacurine and a pinacol rearrangement.

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Section: Figure 1 Mavacuran Alkaloidsmentioning

confidence: 99%

Section: Figure 1 Mavacuran Alkaloidsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Collective Total Synthesis of Mavacuran Alkaloids via an Intermo-lecular 1,4-Addition Approach

Mauger

Jarret

Tap

et al. 2022

Preprint

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“…Indole alkaloids are naturally occurring plant substances that possess a variety of neuropharmacological, psychopharmacological, and antitumor effects [10][11][12][13][14][15][16][17][18]. For example, the alkaloid berberine produces its anticancer effects via the induction of autophagic cell death and mitochondrial apoptosis in cancer cells [19].…”

Section: Introductionmentioning

confidence: 99%

A Novel Mitophagy Enhancer Protects Cardiomyocytes against Hypoxia/Reoxygenation

Yan¹,

Gao²,

Hou³

et al. 2022

Preprint

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Ischemia/reperfusion (I/R) injury results in cell death by inducing apoptosis. During I/R, early generation of mitochondrial reactive oxygen species (mtROS) can induce neighboring mitochondria to release additional ROS, a toxic cycle resulting in significant mitochondrial and cellular injury. Oxidative damage in the mitochondria contributes to various pathologies, including I/R injury. Accordingly, preventing mitochondrial oxidative damage should be therapeutically relevant for many disorders, including cardiovascular diseases. We recently discovered an Indole-Peptide-Tempo Conjugate (IPTC) that served as a novel bifunctional agent with both antioxidant and autophagy-modulating capacity. Here, we demonstrate that IPTC can protect H9C2 cardiomyocytes from hypoxia/reoxygenation (H/R) injury that results from mtROS overproduction due to impaired mitophagy and resultant mitochondrial dysfunction. We hypothesize that the mechanism of action of IPTC involves the capacity to decrease mtROS combined with induction of mitophagy.

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Collective Total Synthesis of Mavacuran Alkaloids through Intermolecular 1,4‐Addition of an Organolithium Reagent**

et al. 2023

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We report a synthetic endeavor towards the highly strained pentacyclic caged framework of the mavacuran alkaloids which culminated with the concise total synthesis of C‐fluorocurine, C‐profluorocurine, C‐mavacurine, normavacurine, 16‐epi‐pleiocarpamine and taberdivarine H. We designed a strategy involving late‐stage construction of the D ring by Michael addition of a vinylic nucleophile to a 2‐indolyl acrylate moiety. While the intramolecular Michael addition did not succeed, we were able to perform a diastereoselective unusual intermolecular 1,4‐addition of a functionalized vinyl lithium reagent to a readily accessible Michael acceptor with the assistance of the piperidine nitrogen atom through the formation of a complex as suggested by DFT computations. Final cyclization was achieved by nucleophilic substitution to form an ammonium intermediate. The first total syntheses of C‐profluorocurine and C‐fluorocurine were finalized by the dihydroxylation of C‐mavacurine and a pinacol rearrangement, respectively.

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The chemistry of mavacurane alkaloids: a rich source of bis-indole alkaloids

Abstract: This review presents the chemistry of mavacuranes, a subfamily of the monoterpene indole alkaloids, from their isolation, biosynthesis, total synthesis to their tendency to assemble with other partners to form intricate bis-indole alkaloids.

Cited by 20 publications

References 152 publications

Collective Total Synthesis of Mavacuran Alkaloids via an Intermo-lecular 1,4-Addition Approach

Collective Total Synthesis of Mavacuran Alkaloids via an Intermo-lecular 1,4-Addition Approach

A Novel Mitophagy Enhancer Protects Cardiomyocytes against Hypoxia/Reoxygenation

Collective Total Synthesis of Mavacuran Alkaloids through Intermolecular 1,4‐Addition of an Organolithium Reagent**

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