Total synthesis of (−)-haploscleridamine

Roy, Moumita Singha; Meng, Xiaofeng; Koda, Karuna; Sivappa, Rasapalli; Gout, Delphine; Lovely, Carl J.

doi:10.1016/j.tetlet.2019.03.004

Cited by 13 publications

(4 citation statements)

References 37 publications

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“…Lovely and co‐workers described the total synthesis of (−)‐haploscleridamine 493 (Scheme 72), a tryptamine‐derived alkaloid extracted from a marine sponge Haplisclerida [253] . The addition of vinylmagnesium bromide to an aldehyde 488 furnished an allylic alcohol 489 , which was then converted to the α , β ‐unsaturated cyclohexanone 491 following two different methods: 1) IBX‐mediated oxidation of 489 resulted an enone 490 which on subsequent RCM with the G‐II catalyst in presence of p ‐TsOH gave 491 in 35% yield; 2) direct ring closing metathesis of 489 with G‐II catalyst furnished a cyclohexanol 492 (81%), which was further converted to 491 via IBX‐oxidation which after several steps provided the desired natural product (−)‐haploscleridamine 493 .…”

Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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The passion of total‐ and fragments syntheses of natural products always remained one of the top priorities among the synthetic chemists worldwide. Due their curiosity toward the complexity of molecules of living nature and their endeavour to imitate them in laboratory; limitless arrays of natural products have been extracted, architecturally‐elucidated, synthesized, and chronicled by utilizing various synthetic methodologies in different fashions. Frequently, the synthesis of complex natural products proceed with inscrutable synthetic challenges, which can be circumvented either by modification of previously developed synthetic methods or by formulating a new one. In this way, a myriad of powerful synthetic reactions have been developed since the genesis of the logic of chemical synthesis. Amongst them, metathesis tactics discovered unexpectedly in the 1950s (Nobel Prize in 2005), have incredibly influenced and changed the landscape of the art of the total and formal synthesis in the last three A. H. Hoveyda, A. R. Zhugralin, me abruptly as compared to other developed transformations or their modified forms. In this particular review article, we envisioned to report a comprehensive detail of the metathetic tools involved in both total and fragments synthesis of natural products in the years 2018 and 2019 along with an overview of 2017.

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Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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“…The plausible reaction mechanism was also investigated by isotopic labeling and real-time NMR experiments, which made two pathways probable. The first asymmetric total synthesis of haploscleridamine (24) was accomplished from histidine (Scheme 12) [126]. The synthesis starts with the tosylation of histidine methyl ester (152), then N-allylation with allyl bromide (154) The first total synthesis of the potential anticancer agent, the β-carboline-vasicinone hybrid alkaloid (±)-peharmaline A (25) was accomplished in a short sequence starting from readily available starting materials (Scheme 13) [127].…”

Section: Co Mementioning

confidence: 99%

“…The first asymmetric total synthesis of haploscleridamine ( 24 ) was accomplished from histidine ( Scheme 12 ) [ 126 ]. The synthesis starts with the tosylation of histidine methyl ester ( 152 ), then N -allylation with allyl bromide ( 154 ) was applied on intermediate 153 leading to compound 155 , followed by a partial ester reduction to afford aldehyde 156 .…”

Section: Natural Products Containing a Simple β-Carboline Skeletonmentioning

confidence: 99%

Recent Advances in the Synthesis of β-Carboline Alkaloids

2021

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β-Carboline alkaloids are a remarkable family of natural and synthetic indole-containing heterocyclic compounds and they are widely distributed in nature. Recently, these alkaloids have been in the focus of interest, thanks to their diverse biological activities. Their pharmacological activity makes them desirable as sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic or antimicrobial drug candidates. The growing potential inherent in them encourages many researchers to address the challenges of the synthesis of natural products containing complex β-carboline frameworks. In this review, we describe the recent developments in the synthesis of β-carboline alkaloids and closely related derivatives through selected examples from the last 5 years. The focus is on the key steps with improved procedures and synthetic approaches. Furthermore the pharmacological potential of the alkaloids is also highlighted.

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“…Among nitrogen-containing heterocyclic systems, the imidazole scaffold is one of the most important and ubiquitously found in a variety of compounds, including natural products, amino acids, proteins, alkaloids, pharmaceutical substances, agrochemicals, and functional materials. 23–36 Additionally, imidazoles have provided an imperative contribution as organocatalysts 37–39 as well as N-heterocyclic carbene in the field of organic synthesis. 40 The synthesis of amino groups containing imidazoles such as 2-aminoimidazole and their derivatives has been widely explored, as they are easy to synthesize directly from guanidine derivatives, particularly following a desulfurization strategy.…”

Section: Introductionmentioning

confidence: 99%