The first highly stereoselective approach to the mitotic kinesin Eg5 inhibitor HR22C16 and its analogues

Xiao, Sen

doi:10.1016/j.tetasy.2009.12.029

Cited by 16 publications

(5 citation statements)

References 40 publications

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“…The same group subsequently utilized a similar chemistry in synthesis of the mitotic kinesin Eg5 inhibitor HR22 C16 and its analogues (Table 3). [76c,d,77] They discovered that cis / trans diastereoselectivity of the CIDT process can be altered by a proper selection of the phenol protecting groups R 2 in the substrates 71 a – d (entries 1–6). Even more interesting and practical was a finding that a stereochemical outcome of the CIDT can in some cases twist by a simple variation of the salts 71 a – h counterion from Cl − to Br − (entries 7,8 and 11,12).…”

Section: Examples Of Cidtmentioning

confidence: 99%

State of the Art in Crystallization‐Induced Diastereomer Transformations

Kolarovič

Jakubec

2021

Adv Synth Catal

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Crystallization-induced diastereomer transformations (CIDT) enable isolation of the target compounds in high enantio-and diastereomeric purities and with up to quantitative yields simply by filtration. Numerous inspiring examples of this appealing synthetic strategy reported over the last fifteen years are reviewed. Important observations along with aspects to consider when designing CIDT experiments are discussed. 3.3. Formation of Schiff Base or Related Intermediates 3.4. Aza-Michael and Mannich-Type Reactions 3.5. Strecker Reaction 3.6. Aldol Reactions 3.7. Epimerization at Phosphorus-Based Stereocenters 3.8. Racemization/Epimerization through Change of Conformation 3.9. Miscellaneous Examples of CIDT 4.Conclusions and Perspectives

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Section: Examples Of Cidtmentioning

confidence: 99%

State of the Art in Crystallization‐Induced Diastereomer Transformations

Kolarovič

Jakubec

2021

Adv Synth Catal

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“…The indole analog was also prepared in the same way. , Otherwise, the ureido derivatives could be prepared by N- activation of the tetrahydroisoquinoline ring with CDI or triphosgene and subsequent addition of an amine before their cyclization into hydantoins (Scheme ). − …”

Section: Fused Hydantoinsmentioning

confidence: 99%

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

et al. 2017

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The review highlights the hydantoin syntheses presented from the point of view of the preparation methods. Novel synthetic routes to various hydantoin structures, the advances brought to the classical methods in the aim of producing more sustainable and environmentally friendly procedures for the preparation of these biomolecules, and a critical comparison of the different synthetic approaches developed in the last twelve years are also described. The review is composed of 95 schemes, 8 figures and 528 references for the last 12 years and includes the description of the hydantoin-based marketed drugs and clinical candidates.

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“…It is worth noting that unprotected or acetyl-protected aldehyde was transformed into the cis-derivative, whereas, benzoyl-or allyl-protected aldehyde afforded the trans-derivative, under the same conditions. Finally, HR22C16, a mitotic kinesin Eg5 inhibitor, could be readily synthesized from the enantiomerically pure (1R,3S)-1,3-disubstituted tetrahydro-β-carboline [41]. This procedure was also efficiently applied to the synthesis of a series of tetrahydro-β-carboline diketopiperazines as single isomers starting from L-tryptophan methyl ester hydrochloride and six aldehydes [42].…”

Section: Starting From Tryptophan Derivativesmentioning

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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The first highly stereoselective approach to the mitotic kinesin Eg5 inhibitor HR22C16 and its analogues

Cited by 16 publications

References 40 publications

State of the Art in Crystallization‐Induced Diastereomer Transformations

State of the Art in Crystallization‐Induced Diastereomer Transformations

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

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

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