Acetonation of l-fucose, l-rhamnose, and 2-deoxy-d-erythro-pentose under kinetically controlled conditions

Barbat, Joēlle; Gelas, Jacques; Horton, Derek

doi:10.1016/0008-6215(83)88122-1

Cited by 20 publications

(21 citation statements)

References 8 publications

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“…The vinyl stannane fragment 6 for the Stille coupling was prepared from the known 2‐deoxy‐ D ‐ribose acetonide6 ( 8 ) (Scheme ). Colvin rearrangement7 using TMS diazomethane and BuLi7c led to the known alkyne 12 8.…”

Section: Resultsmentioning

confidence: 99%

“…Regioselective methylation of the more reactive (non-hydrogen bonded) 4-phenol under Mitsunobu conditions followed by triflate formation provided 5 in multigram scales in Ͼ48 % overall yield. Scheme The vinyl stannane fragment 6 for the Stille coupling was prepared from the known 2-deoxy-d-ribose acetonide [6] (8) (Scheme 2). Colvin rearrangement [7] using TMS diazomethane and BuLi [7c] led to the known alkyne 12.…”

Section: Resultsmentioning

confidence: 99%

“…Trimethylsilyldiazomethane (2.0 M solution in Et 2 O, 0.78 mL, 1.57 mmol) was added dropwise to the above solution and the reaction was stirred for 30 min. This was followed by the addition of a solution of 2‐deoxy‐ D ‐ribose acetonide 8 6 (0.21 g, 1.20 mmol) in anhydrous THF (3 mL) dropwise. The cold bath was removed and a gas outlet was attached as the reaction was warmed to room temp.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis and Biological Studies of a Triazole Analogue of Resorcylic Acid Lactone LL‐Z1640‐2

Goh¹,

Chai²,

Chen³

2014

Eur J Org Chem

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A highly convergent and concise synthesis of a triazole analogue of resorcylic acid lactone natural product LL‐Z1640‐2 has been achieved from easily accessible starting materials in six linear steps in 18 % overall yield. Biological evaluation confirmed the enone system of the natural product is crucial for its activity. The triazole analogue showed good activity (IC50 7.2 μM) against MNK2 kinase, which is an emerging target for cancer chemotherapy.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Biological Studies of a Triazole Analogue of Resorcylic Acid Lactone LL‐Z1640‐2

Goh¹,

Chai²,

Chen³

2014

Eur J Org Chem

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“…Addition of lithium acetylide to propylene oxide followed by silylation of the crude reaction product afforded compound 6. This was then deprotonated (nBuLi) and treated with aldehyde 7, which was readily obtained from d-2-deoxyribose in three steps (acetonide protection, [16] olefination, [17] and oxidation). Benzoate protection of the product afforded the key common intermediate 8 in good overall yield (47 % from propylene oxide).…”

Section: Divergent Synthesis Of Resorcylic Acid Lactones 3 Andmentioning

confidence: 99%

In Vivo Efficacy of Natural Product‐Inspired Irreversible Kinase Inhibitors

et al. 2010

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Hypothemycin and related resorcylic acid lactones (RAL) bearing a cis-enone moiety have emerged as an alternative pharmacophore to heterocyclic motifs for kinase inhibition, and are endowed with a unique selectivity filter based on the irreversible reaction with a subset of the kinome bearing a suitably positioned cysteine residue. Two prototypical examples of "edited" RAL were evaluated for antitumoral, antimetastatic and antiangiogenic efficacy in an orthotopic murine renal cell carcinoma (RENCA) model. Both compounds (3 and 5) are good inhibitors of VEGFRs in vitro, and inhibited tumor growth in vivo with comparable efficacy to sunitinib, an FDA-approved VEGFRs inhibitor. Compound 3 promoted lung metastasis to a similar extent as sunitinib, while compound 5 strongly inhibited lung metastasis. This study attests to the potential of irreversible kinase inhibitors and molecular editing of natural pharmacophores and provides encouraging results to a clinically significant problem.

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“…Intermediate 8, with the iodide masked in the form of a silyl-protected hydroxyl group, was conveniently obtained from acetal-protected deoxyribose [15] in three steps (Scheme 4). Protected deoxyribose (obtained in one step from 2-deoxy-d-ribose) was reduced using LiAlH 4 , and the crude reaction product was selectively silylated on the sterically less encumbered alcohol using TBDPSCl (greater than 15:1 selectivity) in the presence of imidazole in DMF.…”

mentioning

confidence: 99%

Modular Synthesis of Radicicol A and Related Resorcylic Acid Lactones, Potent Kinase Inhibitors

Dakas

Barluenga

Totzke³

et al. 2007

Angew Chem Int Ed

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Short and sweet: A concise and modular synthesis of radicicol A and related resorcylic acid lactones using fluorous isolation technology and immobilized reagents is reported (see scheme, RF=C3H6C6F13, TMSE=2-(trimethylsilyl)ethyl). The compounds are found to be potent (low-nanomolar) inhibitors of selected kinases. Despite their irreversible inactivation of kinases, they show good selectivity amongst a panel of 127 kinases

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Acetonation of l-fucose, l-rhamnose, and 2-deoxy-d-erythro-pentose under kinetically controlled conditions

Cited by 20 publications

References 8 publications

Synthesis and Biological Studies of a Triazole Analogue of Resorcylic Acid Lactone LL‐Z1640‐2

Synthesis and Biological Studies of a Triazole Analogue of Resorcylic Acid Lactone LL‐Z1640‐2

In Vivo Efficacy of Natural Product‐Inspired Irreversible Kinase Inhibitors

Modular Synthesis of Radicicol A and Related Resorcylic Acid Lactones, Potent Kinase Inhibitors

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