The Structure of the Antibiotic Methymycin

Djerassi, Carl; Zderic, John A.

doi:10.1021/ja01593a072

Cited by 50 publications

(10 citation statements)

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“…The racemic trans-2-(tert-butyl)cyclohexanol ((AE)-trans-21) was resolved as a (À)camphanic ester to provide the known (À)-(1R,2S)-and ()-(1S,2R) alcohols 21 [22]. Amazingly, the crystals of the (À)-alcohol (À)-camphanate had cubic-like shapes, whereas the diastereoisomer crystallized as thin needles.…”

Section: Syntheses and Odormentioning

confidence: 99%

“…Finally, we also prepared the 5'-methylated cyclohexane-ring analogs of 19, the −methyl-Ambercore ¾ × 20. Conjugated methyl addition to pulegone and dissolving metal reduction afforded the 1,2-trans : 1,5-cis alcohols 22 [22]. The potassium alcoholates of 22 each reacted with (2S)-and (2R)-2-ethyloxirane 18 to yield the four isomers 20A ± D with enantiomer excesses above 99% and diastereoisomer excesses of 96 ± 98% (Scheme 8).…”

Section: Syntheses and Odormentioning

confidence: 99%

“…Data 1R,2S,5R)). [22] [31]. According to the published protocol [31], ()-(5R)-pulegone was transformed in two steps (1,4-methyl addition, dissolving-metal reduction) to 22.…”

Section: Syntheses and Odormentioning

confidence: 99%

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Amber‐Woody Scent: Alcohols with Divergent Structure Present Common Olfactory Characteristics and Sharp Enantiomer Differentiation

Margot

Simmons

Reichlin

et al. 2004

Helvetica Chimica Acta

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Dedicated to Dr. G¸nther Ohloff on the occasion of his 80th birthday Only one out of the four possible trans isomers of the important perfumery alcohol Norlimbanol ¾ (1) possesses a very strong amber-woody smell, the isomer 1A with (1'R,3S,6'S) absolute configuration. Its enantiomer 1B is almost odorless and devoid of amber-woody character, whereas the diastereoisomers 1C and 1D are considerably weaker and perceptible only by the most-sensitive persons. The same is true for a whole series of perceptual analogs of 1, including b-alkoxy alcohols. These ethers belong to two structural classes: [(2,2,6-trimethylcyclohexyl)oxy]-(see 3, 4, and 16) or {[2-(tert-butyl)cyclohexyl]oxy}alkan-2-ol derivatives (see 19 and 20; Table). A superimposition model allowing for good overlap of the respective hydroxylated side chains offers a tentative explanation for the shared perceptual characteristics of the two classes (Fig. 5). The lipophilic cyclohexane moieties present only a minimal overlap in this model, suggesting that quite larger molecules might possess the same smell. (S)-Configured b-alkoxy alcohols can conveniently be obtained on a larger scale by enantioselective reduction of the corresponding ketones (Scheme 9).

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Section: Syntheses and Odormentioning

confidence: 99%

Section: Syntheses and Odormentioning

confidence: 99%

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Amber‐Woody Scent: Alcohols with Divergent Structure Present Common Olfactory Characteristics and Sharp Enantiomer Differentiation

Margot

Simmons

Reichlin

et al. 2004

Helvetica Chimica Acta

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“…Relatively few 12-membered-ring macrolides have been discovered. The prototype for this small family is methymycin, a compound that has been isolated from cultures of soil micro-organisms such as Streptomyces venezuelae [2]. None of the 12-membered-ring macrolides has yet been found to possess any commercial utility.…”

Section: Classification Of Macrolide Antibioticsmentioning

confidence: 99%

Macrolide antibiotics in food-animal health

Kirst

1997

Expert Opinion on Investigational Drugs

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Several 14- and 16-membered-ring macrolide antibiotics have acquired important roles in the modern production of food animals. Macrolide antibiotics exhibit many similar antimicrobial properties whether used in veterinary or human medicine. In addition to their direct inhibitory action on micro-organisms, macrolides exert a variety of subinhibitory concentration (sub-MIC) effects that are being increasingly recognised as important factors in the explanation of therapeutic results. Macrolides achieve wide tissue distribution and high intracellular concentrations that contribute prominently to their efficacy. Another important factor governing efficacy is the complex interaction between macrolides, micro-organisms, and phagocytes that may enable the host defence system to enhance the antibiotic's inhibitory action. A potential role for macrolides in modulating inflammatory processes has also been recognised. In both sub-MIC effects and interactions with the host immune system, different macrolides exert different responses that may reinforce or oppose each other. This complexity of responses requires additional studies in appropriate disease states and animal species in order to elucidate a more comprehensive understanding and explanation of in vivo outcomes.

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“…Methymycin was the first macrolide to be chemically characterised (Fig. 4) (DJERASSI and ZDERIC, 1956). Methymycin has an antibacterial spectrum similar to but less active, weight for weight, than other macrolide antibiotics (Table 2) (DoNIN et al, 1953/54).…”

Section: Methymycin and Lancamycinmentioning

confidence: 99%

Antibiotics

1967

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AII rights, especially that of tnmslation into foreign languages, reserved. It is also forbidden to reproduce this book, either whole DedicationFor most areas of scientific pursuit, there is usually that rare investigator who has the imagination to conceive ideas, who has faith in his visions, and who has the ability to critically test his concepts in the laboratory. Almost invariably, this scientist also inspires younger men to enthusiastically enter into his research program. To him should go the accolades and the recognitions of the esteem in which he is held. As only a small part of this esteem, we wish to dedicate these books to Professor SELMAN A. W AKSMAN in appreciation of his leadership and contributions in all facets of antibiotic research. PrefaceThe idea for publishing these books on the mechanism of action and on the biosynthesis of antibiotics was born of frustration in our attempts to keep abreast of the literature. Gone were the years when we were able to keep a bibliography on antibiotics and feel confident that we could find everything that was being published on this subject. These fields of investigation were moving forward so rapidly and were encompassing so wide a range of specialized areas in microbiology and chemistry that it was almost impossible to keep abreast of developments. In our naivete and enthusiasm, however, we were unaware that we were toying with an idea that might enmesh us, that we were creating an entity with a life of its own, that we were letting loose a Golom who instead of being our servant would be our master.That we set up ideals for these books is obvious; they would be current guides to developments and information in the areas of mechanism of action and biosynthesis of antibiotics. For almost every subject, we wished to enlist the aid of an investigator who himself had played a part in determining the nature of the phenomena that were being discussed. One concept for the books was that they include only antibiotics for which a definitive, well-documented mechanism of action or biosynthetic pathway was known. Yet, such an approach would not entirely serve the purpose we projected, for it would not encompass all of the information available in these fields of antibiotic investigations and blind searches for the original literature would still have to be made. We therefore chose to include any and all antibiotics about which some pertinent information had been published. It was obvious even at the start that such a compilation, integration, and analysis of information could never be complete unless scientific investigations ceased at the moment the last manuscript was submitted-an end that was neither desirable nor possible. An addendum was therefore included at the end of the volume and left open for the addition of new information until the last pages of the regular articles had been printed.The original concept has also been further expanded as the authors of several papers found it advisable to elaborate on their subject. Some of the articles included discussions...

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The Structure of the Antibiotic Methymycin

Cited by 50 publications

References 2 publications

Amber‐Woody Scent: Alcohols with Divergent Structure Present Common Olfactory Characteristics and Sharp Enantiomer Differentiation

Amber‐Woody Scent: Alcohols with Divergent Structure Present Common Olfactory Characteristics and Sharp Enantiomer Differentiation

Macrolide antibiotics in food-animal health

Antibiotics

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