Stereoselective synthesis of (−)-desethyleburnamonine, (−)-vindeburnol and (−)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction

Mondal, Pravat; Argade, Narshinha P.

doi:10.1039/c6ob01438k

Cited by 17 publications

(1 citation statement)

References 26 publications

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“…26,27 (+)-Rhodoconferimide exhibits a 15-fold more potent free radical scavenging activity compared to the well-known synthetic antioxidant 2,6-di-tert-butyl-4-methylphenol (BHT) (Figure 1). 26 In continuation of our studies on the total synthesis of recently isolated structurally interesting and biologically important natural products; [28][29][30] we herein report the first total synthesis of (±)-rhodoconferimide from the readily available precursors vanillin and dimethyl maleate.…”

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confidence: 94%

First Total Synthesis of (±)-Rhodoconferimide

Pandhade

Argade

2017

Synthesis

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mentioning

confidence: 94%

First Total Synthesis of (±)-Rhodoconferimide

Pandhade

Argade

2017

Synthesis

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Catalytic Asymmetric Alkynylation of 3,4‐Dihydro‐β‐carbolinium Ions Enables Collective Total Syntheses of Indole Alkaloids

et al. 2021

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Chiral tetrahydro-b-carboline (THbC) is not only ap revailing structural feature of many natural alkaloids but also av ersatile synthetic precursor for av ast arrayo f monoterpenoid indole alkaloids.Asymmetric synthesis of C1alkynyl THbCs remains rarely explored and challenging. Herein, we describe the development of two complementary approaches for the catalytic asymmetric alkynylation of 3,4dihydro-b-carbolinium ions with up to 96 %yield and 99 %ee. The utility of chiral C1-alkynyl THbCs was demonstrated by the collective total syntheses of seven indole alkaloids: harmicine,eburnamonine,desethyleburnamonine,larutensine, geissoschizol, geissochizine,and akuammicine.

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Stereodivergent Total Synthesis of Tacaman Alkaloids

Chen,

Wang,

Zeng

et al. 2024

Angewandte Chemie

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This paper describes a concise, asymmetric and stereodivergent total synthesis of tacaman alkaloids. A key step in this synthesis is the biocatalytic Baeyer‐Villiger oxidation of cyclohexanone, which was developed to produce seven‐membered lactones and establish the required stereochemistry at the C14 position (92% yield, 99% ee, 500 mg scale). Cis‐ and trans‐tetracyclic indoloquinolizidine scaffolds were rapidly synthesized through an acid‐triggered, tunable acyl‐Pictet‐Spengler type cyclization cascade, serving as the pivotal reaction for building the alkaloid skeleton. Computational results revealed that hydrogen bonding was crucial in stabilizing intermediates and inducing different addition reactions during the acyl‐Pictet‐Spengler cyclization cascade. By strategically using these two reactions and the late‐stage diversification of the functionalized indoloquinolizidine core, the asymmetric total syntheses of eight tacaman alkaloids were achieved. This study may potentially advance research related to the medicinal chemistry of tacaman alkaloids.

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Stereoselective synthesis of (−)-desethyleburnamonine, (−)-vindeburnol and (−)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction

Cited by 17 publications

References 26 publications

First Total Synthesis of (±)-Rhodoconferimide

First Total Synthesis of (±)-Rhodoconferimide

Catalytic Asymmetric Alkynylation of 3,4‐Dihydro‐β‐carbolinium Ions Enables Collective Total Syntheses of Indole Alkaloids

Stereodivergent Total Synthesis of Tacaman Alkaloids

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