Stereocontrolled total synthesis of dl-gibberellin A15

Nagata, Wataru; Wakabayashi, T.; Narisada, Masayuki; Hayase, Yoshio; Kamata, Satsuo

doi:10.1021/ja00751a028

Cited by 34 publications

(22 citation statements)

References 2 publications

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“…Rather, a protected form of the carboxylate must be maintained during monolayer formation. [44][45][46] The SAM is stable under these Scheme 1. Unlike more reactive functional groups such as acid chloride, 33 the methyl ester group can survive the process of trichlorosilane anchoring to the surface.…”

Section: Introductionmentioning

confidence: 99%

Interfacial chemistry on carboxylate‐functionalized monolayer assemblies

Gershevitz

Osnis

Sukenik

2005

Israel Journal of Chemistry

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Deposition of trichlorosilanes with ester groups at their remote termini provides a convenient entry to carboxylic acid‐bearing siloxane‐anchored self‐assembled monolayers. The de‐esterification of these esters has been optimized to minimize monolayer damage, and their quantitative re‐esterification provides clear evidence for the stability of these systems. Both the structure of the ester‐terminated monolayer and its de‐esterification/esterification chemistry can be easily monitored by FTIR‐ATR measurements. This spectroscopic tool, together with a liquid cell that enables IR spectra to be measured in an aqueous environment, enables a detailed structural analysis of the carboxylic acid‐bearing siloxane‐anchored self‐assembled monolayers and an assessment of their acid/base behavior (by in situ titration). The use of D2O instead of H2O for the in situ titration experiments also improves the available IR window. Both monomeric and dimeric/oligomeric acid groups are seen, and the relative ease of deprotonation of these various species can be directly monitored. Monomers of alkyl carboxylic acids that are hydrogen bonded only to surrounding water molecules have a pKa = 4.9, while the pKa for the aggregated molecules is 9.3. Similar behavior is seen for surface‐bound benzoic acids, where the two pKa values are 4.7 and 9.0. The influence of temperature on these structures and their chemistry has been explored to a limited extent as well. When the alkylcarboxylic acid system is cooled to 10 °C, the pKa value for the acid monomers is reduced from 4.9 to 4.5 and increases from 9.3 to 10.3 for the aggregates.

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Section: Introductionmentioning

confidence: 99%

Interfacial chemistry on carboxylate‐functionalized monolayer assemblies

Gershevitz

Osnis

Sukenik

2005

Israel Journal of Chemistry

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“…In gibberellin research, Kurosawa proved that small biofunctional molecules produced by G. fujikuroi caused the elongation of rice seedlings. In the case of the gibberellins, their synthesis was undertaken by many groups, culminating in total synthesis by Nagata, 5 Corey, 6 Mander,7,8 Yamada and Nagaoka, 9 Ihara and Toyota, 10 and others. In 1938, Yabuta and Sumiki isolated the plant hormone gibberellins as crude crystals, which elongated rice seedlings.…”

Section: Vitaminsmentioning

confidence: 99%

Introduction—Biofunctional Molecules and Organic Synthesis

Mori

2010

Chemical Synthesis of Hormones, Pheromones and Other Bioregulators

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“…The use of anisoles (22) as synthetic equivalents to cyclohex-2-enones (Scheme 3) has been widespread since the original observations of Birch, and the literature is replete with examples over the past five decades, e.g. in the syntheses of steroids,2 terpenoids 6 and alkaloids.…”

Section: Benzenoid Hydrocarbons and Ethersmentioning

confidence: 99%

Partial Reduction of Aromatic Rings by Dissolving Metals and by Other Methods

Mander

1991

Comprehensive Organic Synthesis

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Stereocontrolled total synthesis of dl-gibberellin A15

Cited by 34 publications

References 2 publications

Interfacial chemistry on carboxylate‐functionalized monolayer assemblies

Interfacial chemistry on carboxylate‐functionalized monolayer assemblies

Introduction—Biofunctional Molecules and Organic Synthesis

Partial Reduction of Aromatic Rings by Dissolving Metals and by Other Methods

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