Enantioselective Epoxidation of Allylic Alcohols: (2
            <i>S</i>
            ,3
            <i>S</i>
            )‐3‐Propyloxiranemethanol

Hill, J. Gordon; Sharpless, K. Barry; Exon, Christopher; Regenye, R. W.

doi:10.1002/0471264180.os063.08

Cited by 15 publications

(24 citation statements)

References 7 publications

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“…Procedures to prepare anhydrous TBHP in dichloromethane or toluene have been reported earlier. 9 , 10 However, these procedures involve azeotropic distillation, which needs to be carried out behind a blast shield in a well-ventilated fume hood because of the flammable and explosive nature of TBHP. 11 The safety concerns associated with azeotropic distillation on a large scale led us to devise a simpler procedure to obtain anhydrous TBHP.…”

Section: Antecedents and Resultsmentioning

confidence: 99%

Development of a Scalable Process for the Synthesis of DNDI-VL-2098: A Potential Preclinical Drug Candidate for the Treatment of Visceral Leishmaniasis

Satam¹,

Pedada²,

Kamaraj³

et al. 2016

Org. Process Res. Dev.

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A process suitable for kilogram-scale synthesis of (2R)-2-methyl-6-nitro-2-{[4-(trifluoromethoxy)phenoxy]methyl}-2,3-dihydroimidazo[2,1-b][1,3]oxazole (DNDI-VL-2098, 2), a preclinical drug candidate for the treatment of visceral leishmaniasis, is described. The four-step synthesis of the target compound involves the Sharpless asymmetric epoxidation of 2-methyl-2-propen-1-ol, 8. Identification of a suitable synthetic route using retrosynthetic analysis and development of a scalable process to access several kilograms of 2 are illustrated. The process was simplified by employing in situ synthesis of some intermediates, reducing safety hazards, and eliminating the need for column chromatography. The improved reactions were carried out on the kilogram scale to produce 2 in good yield, high optical purity, and high quality.

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Section: Antecedents and Resultsmentioning

confidence: 99%

Development of a Scalable Process for the Synthesis of DNDI-VL-2098: A Potential Preclinical Drug Candidate for the Treatment of Visceral Leishmaniasis

Satam¹,

Pedada²,

Kamaraj³

et al. 2016

Org. Process Res. Dev.

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“…Thioesterification of 20 gave octanoylthiolide dienol 21 . However, mono-epoxidation of 21 under Shapless conditions 17 failed to afford the desired epoxyalcohol 22 . The thioester suffered cleavage during the reaction, and both the liberated thiol and isopropanol from the epoxidation catalyst formation participated in opening of the epoxide to give a complex mixture of undesired products.…”

Section: Resultsmentioning

confidence: 99%

Total Syntheses of the Histone Deacetylase Inhibitors Largazole and 2-epi-Largazole: Application of N-Heterocyclic Carbene Mediated Acylations in Complex Molecule Synthesis

et al. 2011

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Details of the evolution of strategies toward convergent assembly of the histone deacetylase inhibiting natural product largazole exploiting γ,δ-unsaturated-α,β-epoxy-aldehydes and a thiazole-thiazoline containing ω-amino-acid are described. The initial N-heterocyclic carbene mediated redox amidation exploying these two types of building blocks representing largazole’s structural domains of distinct biosynthetic origin directly afforded the seco-acid of largazole. This was accomplished without any protecting groups resident upon either thioester bearing epoxy-aldehyde or the tetrapeptide. However, the ineffective production of largazole via the final macrolactonization led to an alternative intramolecular esterification/macrolactamization strategy employing the established two building blocks. This provided largazole along with its C2-epimer via an unexpected inversion of the α-stereocenter at the valine residue. The biological evaluation demonstrated that both largazole and 2-epi-largazole led to dose-dependent increases of acetylation of histone H3, indicating their potencies as class I histone deacetylase selective inhibitiors. Enhanced p21 expression was also induced by largazole and its C2 epimer. In addition, 2-epi-largazole displayed more potent activity than largazole in cell viability assays against PC-3 and LNCaP prostate cancer cell lines.

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“…The resultant dry TBHP solution was stored under nitrogen at 0°C and its concentration was calculated from 1 H NMR spectroscopic analysis. [41,42] TLC analysis was performed using Merck 5554 aluminium backed plates. Compounds were visualised using UV (254 nm) light, iodine, vanillin or a basic aqueous solution of potassium permanganate, where appropriate.…”

Section: Methodsmentioning

confidence: 99%

The Epoxy‐Ramberg–Bäcklund Reaction (ERBR): A Sulfone‐Based Method for the Synthesis of Allylic Alcohols

2006

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Enantioselective Epoxidation of Allylic Alcohols: (2 S ,3 S )‐3‐Propyloxiranemethanol

Abstract: Enantioselective epoxidation of allylic alcohols: (2 S ,3 S )‐3‐propyloxiranemethanol product: (2 S ,3 S )‐3‐propyloxiranemethanol

Cited by 15 publications

References 7 publications

Development of a Scalable Process for the Synthesis of DNDI-VL-2098: A Potential Preclinical Drug Candidate for the Treatment of Visceral Leishmaniasis

Development of a Scalable Process for the Synthesis of DNDI-VL-2098: A Potential Preclinical Drug Candidate for the Treatment of Visceral Leishmaniasis

Total Syntheses of the Histone Deacetylase Inhibitors Largazole and 2-epi-Largazole: Application of N-Heterocyclic Carbene Mediated Acylations in Complex Molecule Synthesis

The Epoxy‐Ramberg–Bäcklund Reaction (ERBR): A Sulfone‐Based Method for the Synthesis of Allylic Alcohols

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