Enantiospecific gram scale synthesis of (S)-eleagnine

Lood, Christopher S.; Nieger, Martin; Koskinen, Ari M. P.

doi:10.1016/j.tet.2015.05.063

Cited by 11 publications

(10 citation statements)

References 49 publications

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“…In 2015, Lood et al reported the new enantiospecific gram-scale synthesis of ( S )-eleagnine/(−)-tetrahydroharmane ( 2 ) ( Scheme 2 ) [ 110 ]. Their synthesis started from the previously modified amino acid methyl ester 82 , which included the appropriate chirality.…”

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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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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“…Phenanthroindolizidines (50 [71,72]), phenanthroquinolizidines (51 [72]), tetrahydroprotoberberines (53 [67,68]), pyrroloisoquinolines (55 [69,70]), and diketopiperazine-fused THIQs (65 [73], vide infra) embody the tetrahydroisoquinoline skeleton, while indolizinoindoles (57 [74,75]), THBC-imidazolinediones (59 [76]), THBC-piperazinedione (61 [77,78]), the tetracyclic indole alkaloids (S)-harmicine (pyrrole-fused THBC, [66,79]), and (S)-eleagnine (1-methyl THBC, [66,80] represent the THBC-containing polyheterocycles. The additional ring can be already present in the imine substrate before the P-S reaction (type A) or can be built on the THIQ/THBC skeleton exploiting the functionality of some substituents (type B).…”

Section: Polyheterocyclesmentioning

confidence: 99%

The Pictet-Spengler Reaction Updates Its Habits

et al. 2020

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The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) following its centenary birthday, the P-S reaction did not exit the stage but it came up again on limelight with new features. This review focuses on the interesting results achieved in this period (2011–2015), analyzing the versatility of this reaction. Classic P-S was reported in the total synthesis of complex alkaloids, in combination with chiral catalysts as well as for the generation of libraries of compounds in medicinal chemistry. The P-S has been used also in tandem reactions, with the sequences including ring closing metathesis, isomerization, Michael addition, and Gold- or Brønsted acid-catalyzed N-acyliminium cyclization. Moreover, the combination of P-S reaction with Ugi multicomponent reaction has been exploited for the construction of highly complex polycyclic architectures in few steps and high yields. The P-S reaction has also been successfully employed in solid-phase synthesis, affording products with different structures, including peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the enzymatic version of P-S has been reported for biosynthesis, biotransformations, and bioconjugations.

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“…The synthesis contemplated the de novo construction of the indole ring with the appropriate substituents to give the PSR in the final step. A gram-scale total synthesis of (S)-eleagnine [53] and (S)-harmicine [54] in enantiopure form (>99% ee) was achieved.…”

Section: Chiral Auxiliariesmentioning

confidence: 99%

The Chiral Pool in the Pictet–Spengler Reaction for the Synthesis of β-Carbolines

Dalpozzo

2016

Molecules

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Abstract:The Pictet-Spengler reaction (PSR) is the reaction of a β-arylethylamine with an aldehyde or ketone, followed by ring closure to give an aza-heterocycle. When the β-arylethylamine is tryptamine, the product is a β-carboline, a widespread skeleton in natural alkaloids. In the natural occurrence, these compounds are generally enantiopure, thus the asymmetric synthesis of these compounds have been attracting the interest of organic chemists. This review aims to give an overview of the asymmetric PSR, in which the chirality arises from optically pure amines or carbonyl compounds both from natural sources and from asymmetric syntheses to assemble the reaction partners.

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Enantiospecific gram scale synthesis of (S)-eleagnine

Abstract: a b s t r a c tAn alternative route to the tetrahydro-b-carboline scaffold is presented, where the amino acid L-alanine was transformed to (S)-eleagnine in a straightforward and scalable manner yielding the target compound in enantiopure form on gram scale.

Cited by 11 publications

References 49 publications

Recent Advances in the Synthesis of β-Carboline Alkaloids

Recent Advances in the Synthesis of β-Carboline Alkaloids

The Pictet-Spengler Reaction Updates Its Habits

The Chiral Pool in the Pictet–Spengler Reaction for the Synthesis of β-Carbolines

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