Cyclopropanonhydrat

Grewe, Rudolf; Struve, Alfred

doi:10.1002/cber.19630961041

Cited by 28 publications

(17 citation statements)

References 15 publications

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“…C14-H 2 , N 0 2 requires M , 235.1572); v,,,(CHCl,)/cm-' 3600, 3400, 1495,1470,1455,1390,1375,1280,1240,1110 and 1060; ~3~0.65-1.05 (6 H, m), 1.32-1.60 (3 H, m), 2.362.48 (2 H, m), 2.95-3. 45 (1 H, m), 4.25 (1 H, q, J 6.5), 5.35-5.75 (1 H, m) and 7.35 (5 H, m).…”

Section: -Isopropyl-n-[(r)-a-methylbenzylisoxazolidin-5-01 32a-mentioning

confidence: 99%

Asymmetric syntheses of the naturally occurring β-amino acids, β-lysine, β-leucine and β-phenyl-β-alanine via nitrone cycloaddition

Keirs¹,

Moffat²,

Overton³

et al. 1991

J. Chem. Soc., Perkin Trans. 1

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Section: -Isopropyl-n-[(r)-a-methylbenzylisoxazolidin-5-01 32a-mentioning

confidence: 99%

Asymmetric syntheses of the naturally occurring β-amino acids, β-lysine, β-leucine and β-phenyl-β-alanine via nitrone cycloaddition

Keirs¹,

Moffat²,

Overton³

et al. 1991

J. Chem. Soc., Perkin Trans. 1

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“…Diethyl ketene acetal was purchased from Fluka, and distilled prior to use. Ketene-[o-xylyleneacetal] was prepared as described in the literature [13]. Pentacarbonyl-[(1R,2S,5R)-(À)-menthyloxybenzylidene]-chromium (0) and [(1R,2S,5R)-(À)-phenylmenthyloxybenzylidene]-chromium (0) were prepared as described by Dötz and Stinner [14].…”

Section: Methodsmentioning

confidence: 99%

“…Recrystallization from pentane provides purple needles, mp 88-90°C (sharp). 1 H NMR (300 MHz, CDCl 3 ) d 1.57 (d, 6 H, CH(CH 3 ) 2 , J = 6.0 Hz), 6.00 (sept, 1H, CH(CH 3 ) 2 ), 6.59 (bs, 1H, CH-2), 7.04 (d, 1H, CH-3, J = 2.7 Hz), 7.89 (s, 1H, CH-1); 13 3.6. Pentacarbonyl-[1-isopropoxy-n-pentylidene]-chromium (0) (18c)…”

Section: Pentacarbonyl-[isopropoxy-2-furanyl-methylidene]-chromium (0mentioning

confidence: 98%

“…int.) 320 M + (7), 292 (13), 264 (9), 236 (5) 6, 25.9, 28.3, 71.3, 86.8, 216.5, 223.5, 357.3;IR (film) 590, 648, 666, 853, 914, 982, 1062IR (film) 590, 648, 666, 853, 914, 982, , 1100IR (film) 590, 648, 666, 853, 914, 982, , 1258IR (film) 590, 648, 666, 853, 914, 982, , 1325IR (film) 590, 648, 666, 853, 914, 982, , 1368IR (film) 590, 648, 666, 853, 914, 982, , 1443IR (film) 590, 648, 666, 853, 914, 982, , 1916IR (film) 590, 648, 666, 853, 914, 982, , 2080IR (film) 590, 648, 666, 853, 914, 982, , 2857IR (film) 590, 648, 666, 853, 914, 982, , 2934 …”

Section: Pentacarbonyl-[isopropoxy-2-furanyl-methylidene]-chromium (0mentioning

confidence: 99%

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The first synthesis of cyclopropanone acetals from the reaction of Fischer carbene complexes with ketene acetals

Wang

Goldberg

Liu

et al. 2005

Journal of Organometallic Chemistry

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“…This can be rationalized in present-day terms by assuming that the initially formed carbocation in any of these cyclizations needs to undergo a 1,2 hydride shift prior to ring closure. That leading to 10 gives greater separation between the charge on carbon and that on the protonated side chain amino group in the intermediate to 11. Repetition of the experiment that led to the dialkylated product 8 starting with the allyl derivative 15 surprisingly led to a product, 20, that contained the carbocyclic equivalent of the morphine ring system (11).…”

mentioning

confidence: 99%

Evolution of the morphinan synthesis

Lednicer¹

1989

J. Chem. Educ.

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One of the earliest and longest lasting targets for medicinal chemists has been the relief of pain. Most of the central analgetics, though quite effective, present a serious drawback in that they often lead to addiction. A considerable amount of effort has thus been devoted toward attempts to produce structural analogues. Morphinans such as levallorphan, 1, and benzomorphans such as pentazocine, 2, which are essentially abbreviated versions of morphine and are but single representatives of very large series of analogues, do show reduced addiction potential. The key reaction to the preparation of these structures is the Grewe carbocation cyclization.The original central analgetic agent, morphine, 3, was first isolated from opium, the dried sap from the seed pod of Papaver somniferum, in pure crystalline form by Serturner as early as 1803. Structural proposals by Robinson (1) and by Schopf (2) followed 120 years later, after organic chemistry had developed sufficiently to tackle complex molecules. Grewe's research led to the first synthesis for the morphine skeleton and also provided the first generalized entry to simplified analogues of morphine.

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Cyclopropanonhydrat

Abstract: Cyclopropanonhydrat (VII) wird nach einem neuen Prinzip auf dem Wege über das Keten‐[o ‐oxylylenacetal] (V) synthetisiert.

Cited by 28 publications

References 15 publications

Asymmetric syntheses of the naturally occurring β-amino acids, β-lysine, β-leucine and β-phenyl-β-alanine via nitrone cycloaddition

Asymmetric syntheses of the naturally occurring β-amino acids, β-lysine, β-leucine and β-phenyl-β-alanine via nitrone cycloaddition

The first synthesis of cyclopropanone acetals from the reaction of Fischer carbene complexes with ketene acetals

Evolution of the morphinan synthesis

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