[2+2] Photoadditions with chiral 2,5-cyclohexadienone synthons

Lange, Gordon L.; Humber, Craig C.; Manthorpe, Jeffrey M.

doi:10.1016/s0957-4166(02)00339-7

Cited by 9 publications

(8 citation statements)

References 18 publications

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“…Therefore, compound 2 was identified as 1-(2′,4′-dihydroxy-phenyl)-5-methyl-7-[2,2,5-trimethyl-5-(4-methyl-pent-3-enyl)- [1,3]dioxolan-4-yl]-hept-4-en-1-one and was given the trivial name 8,9-oxoisopropanyldshamirone. As mentioned above, compound 2 was also synthesized from 1 by the chemical transformation [12] (l " Fig. 2), which further confirmed its structural elucidation.…”

supporting

confidence: 69%

Antibacterial Sesquiterpenoid Derivatives from Ferula ferulaeoides

Liu

Osman²,

Kaatz

et al. 2013

Planta Med

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Three new sesquiterpenoid derivatives 1, 2, and 3 were isolated from Ferula ferulaeoides. To confirm the structure, compound 2 was also synthesized via a condensation reaction between compound 1 and 2,2-dimethoxypropane. The structures of these three compounds were elucidated by means of spectroscopic and chemical methods. Their antibacterial activity against drug-resistant Staphylococcus aureus strains were evaluated with MIC values in the range of 0.5-128 µg/mL. Compounds 1 and 3 were capable of inhibiting efflux of ethidium bromide using an in vitro assay. The cytotoxicity of the compounds was evaluated on cultured HEK293 cells, and none of them showed toxicity to HEK293 cells at a concentration of 125 µg/mL.

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supporting

confidence: 69%

Antibacterial Sesquiterpenoid Derivatives from Ferula ferulaeoides

Liu

Osman²,

Kaatz

et al. 2013

Planta Med

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“…The yield of acetal-lactone 2a was determined by 1 H NMR [36,37] using mesitylene as an internal standard. The acetalization with pentan-3-one was carried out under the same conditions to obtain acetal-lactone 2b [38].…”

Section: Acetalization Of Quinic Acid (1)mentioning

confidence: 99%

Application of Heterogeneous Catalysts in the First Steps of the Oseltamivir Synthesis

Fraile

Saavedra

2017

Catalysts

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Abstract:The first steps of oseltamivir synthesis from quinic acid involve acetalization and ester formation. These reactions are catalyzed by either acids or bases, which may be accomplished by heterogeneous catalysts. Sulfonic solids are efficient acid catalysts for acetalization and esterification reactions. Supported tetraalkylammonium hydroxide or 1,5,7-triazabicyclo[4.4.0]dec-5-ene are also efficient base catalysts for lactone alcoholysis and in this work, these catalysts have been applied in two alternative synthetic routes that lead to oseltamivir. The classical route consists of an acetalization, followed by a lactonization, and then a lactone alcoholysis. This achieves a 66% isolated yield. The alternative route consists of esterification followed by acetalization and is only efficient when an acetone acetal is used.

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“…This compound was a key molecule in the development of a new route to the sesquiterpene, sterpurene 197 . Lange and coworkers 198 have investigated photoadditions to the chiral 2,5-cyclohexadienone synthons (312). The addition to cyclopentene affords 313 as the major product in the yields shown.…”

Section: Cyclohexenone Cycloadditionsmentioning

confidence: 99%

Photochemistry of Cyclobutanes: Synthesis and Reactivity

Horspool

2009

Patai's Chemistry of Functional Groups

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Introduction Cycloaddition Reactions Involving Alkenes Cycloaddition Reactions Involving Dienes and Trienes Cycloadditions of Enones and Related Compounds Photochemistry of Ketones Cage Compounds Cyclobutane Ring Opening Reactions

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[2+2] Photoadditions with chiral 2,5-cyclohexadienone synthons

Cited by 9 publications

References 18 publications

Antibacterial Sesquiterpenoid Derivatives from Ferula ferulaeoides

Antibacterial Sesquiterpenoid Derivatives from Ferula ferulaeoides

Application of Heterogeneous Catalysts in the First Steps of the Oseltamivir Synthesis

Photochemistry of Cyclobutanes: Synthesis and Reactivity

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