An efficient synthesis of (S)-5-hydroxymethyl-2(5H)-furanone

Vekemans, Jef A. J. M.; Franken, G. A. M.; Chittenden, G. J. F.; Godefroi, Erik F.

doi:10.1016/s0040-4039(00)96107-0

Cited by 18 publications

(4 citation statements)

References 13 publications

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“…Compound 16 had previously been obtained only in one instance as a 6:1 mixture with 13 [18,19] by the reaction of D-ribonolactone with HBA, followed by the reaction with Ac 2 O, and used without purification for further synthetic elaborations. The low-field (60 MHz) 1 H-NMR data reported for 16, obtained from the 16/13 mixture, were limited to the CH 2 OAc group and did not give conclusive information on the structure of 16.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Brominated Lactones Related to Mycalin A: Selective Antiproliferative Activity on Metastatic Melanoma Cells and Inhibition of the Cell Migration

et al. 2023

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Starting from D-xylonolactone and D-ribonolactone, several five-membered bromolactones, related to the C1–C5 portion of mycalin A lactone, have been synthesized. The bromination of D-ribonolactone with HBr/AcOH, without a subsequent transesterification step, has been studied for the first time, giving us most of the acetylated lactones investigated in the present study. For each compound, where possible, both the C-3 alcohol and the corresponding acetate were prepared. Evaluation of their anti-tumor activity showed that all the acetates possess a good cytotoxicity towards human melanoma (A375), human cervical adenocarcinoma (HeLa) and human metastatic melanoma (WM266) cancer cells, comparable or even higher than that displayed by the original mycalin A lactone. Lactone acetates derived from D-ribonolactone showed the higher selectivity of action, exhibiting a strong cytotoxicity on all the tested tumor cells but only a limited toxicity on healthy human dermal fibroblast (HDF) cells, used as a control. Wound healing assays showed that two of these substances inhibit the migration of the WM266 cells.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Brominated Lactones Related to Mycalin A: Selective Antiproliferative Activity on Metastatic Melanoma Cells and Inhibition of the Cell Migration

et al. 2023

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“…Also starting from D-ribonolactone, Vekemans et al described a three-step synthesis in 48% yield on multigram scale (Scheme 1c). 10 Treatment of the carbohydrate with HBr in acetic acid provided acetylated bromo-deoxyaldono-1,4-lactone, 3 or 3'. Then, the NaHSO3-mediated elimination of the acetate and bromide moieties led to the unsaturated lactone, 4 or 4', that was finally hydrolyzed under acidic conditions to provide HBO.…”

Section: Syntheses Of Hbomentioning

confidence: 99%

“…After treatment with Raney nickel, tritylated HBO ( HBO-Tr ) was obtained in 51% yield on a multigram scale. Also starting from d -ribonolactone, Vekemans et al described a three-step synthesis in 48% yield on a multigram scale (Scheme c) . Treatment of the carbohydrate with HBr in acetic acid provided acetylated bromodeoxyaldono-1,4-lactone 3 or 3′ .…”

Section: Syntheses Of Hbomentioning

confidence: 99%

(S)-γ-Hydroxymethyl-α,β-butenolide, a Valuable Chiral Synthon: Syntheses, Reactivity, and Applications

Flourat

Haudrechy

Allais

et al. 2019

Org. Process Res. Dev.

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Chirality is greatly sought for pharmaceutical compounds or fragrance and flavors.(S)-γ-hydroxymethyl-α,β-butenolide, aka HBO, is a chiral (5H)-furanone providing a polarized double bond, a lactone ring and a primary alcohol as playground for synthetic chemists. This molecule has been used for forty years in a wide range of synthetic pathways to natural and/or bioactive molecules. Its own synthesis, always from biosourced product, has also significantly evolved and could be now achieved both at large scale and by applying Green Chemistry principles. This review will explore the syntheses, the reactivity and the uses of HBO.

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“…A synthesis from L-glutamic acid involved introduction of a double bond by selenium chemistry.174 Another used the D-glyceraldehyde derivative153 which can be prepared from D-mannitol 175. The other three started with D-ribonolactone, and 150 was prepared by pyrolysis of the cyclic orthoformate 154,152 by Raney nickel reduction of the cyclic thiocarbonate 155,176 or by the NaHS03-induced elimination of the bromoacetate 156 177. The susceptibility of the butenolide150 to racemization is a drawback of this strategy.155method utilizing Michael additions to a,0-unsaturated sugar aldehydes has also been developed.…”

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confidence: 99%