Oxydations par le carbonate d'argent sur celite—XIII

Fétizon, M.; Golfier, M.; Louis, J-M.

doi:10.1016/0040-4020(75)85013-7

Cited by 117 publications

(34 citation statements)

References 24 publications

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“…In contrast to the preparation of 24, it was necessary in this instance to isolate the intermediate enol phosphate, as the Me 2 CuLi treatment proceeded only incompletely otherwise. Reduction of 28 to [ 2 H 3 ]farnesol (29) and pyrophosphoric acid esterification of the chloride 30 to give 31 were carried out as described for [ 2 H 3 ]geraniol (25).…”

mentioning

confidence: 99%

Stereochemistry of Formation of theβ-Ring of Lycopene: Biosynthesis of (1R,1′R)-β,β-[16,16,16,16′,16′,16′-2H6]Carotene from [16,16,16,16′,16′,16′-2H6]Lycopene inFlavobacterium R 1560

Mohanty

Uebelhart

Eugster

2000

HCA

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Dedicated to Prof. Albert Eschenmoser on the occasion of his 75th birthday Incubation of deuteriated precursors in cultures of Flavobacterium produced specifically deuteriated carotenoids. Analysis of these led to several conclusions: i) Lycopene is a direct precursor of b,b-carotene. ii) Its terminal Me groups retain their integrity during cyclization: there is a stereospecific folding of the 1,5-diene. The Me(16,16') groups of lycopene become the Me(16,16') of b,b-carotene. Consequently, the folding must follow the C 2 (E,E) mode. iii) Incorporation of deuterium was sufficiently extensive to permit CD measurements on the isolated b,b-carotene, allowing its centers of chirality to be assigned as (1S,1'S). iv) The same chirality resulted from incorporation of [ 2 H 3 ]mevalonate into zeaxanthin. The syntheses of specifically deuteriated [ 2 H 3 ]GPP, [ 2 H 3 ]FPP, and [ 2 H 3 ]GG are described.

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confidence: 99%

Stereochemistry of Formation of theβ-Ring of Lycopene: Biosynthesis of (1R,1′R)-β,β-[16,16,16,16′,16′,16′-2H6]Carotene from [16,16,16,16′,16′,16′-2H6]Lycopene inFlavobacterium R 1560

Mohanty

Uebelhart

Eugster

2000

HCA

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“…13 (4)); 2.12 ± 1.93 (m, CH 2 (6)); 1.92 ± 1.66 (m, CH 2 (5)); 1.74 (s, Me (7) 3S,3aS,7aR)-and (3R,3aR,7aS)-2,3,3a,4,5,7a-Hexahydro-3,6-dimethylbenzofuran; (À)-and ()-6, resp.) and ()-(3R,4S,8R)-and (À)-(3S,4R,8S)-3,9-Epoxy-p-menth-1-ene ( (3R,3aS,7aR)-and (3S,3aR,7aS)-2,3,3a,4,5,7a-Hexahydro-3,6-dimethylbenzofuran; ()-and (À)-15, resp.).…”

Section: ()-(3r4r)-and (à)-(3s4smentioning

confidence: 97%

“…Pyridinium chlorochromate (PCC) gave mainly 4, whilst MnO 2 in the same solvent showed reverse selectivity. Even though the reagent Ag 2 CO 3 on Celite [13] was described as an Scheme 1. Retrosynthetic Analysis Scheme 2 excellent chemoselective oxidant for the preparation of butenolides starting from 1,4 diols [14], we observed that the latter reagent was fairly superior to MnO 2 .…”

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confidence: 99%

“…All moisture-sensitive reactions were carried out under a static atmosphere of N 2 . All reagents were of commercial quality, with the exception of Ag 2 CO 3 on Celite, −o-iodoxybenzoic acid× (IBX), DessÀMartin periodinane (DMP), and hydridotetrakis(triphenylphosphine)rhodium, which were prepared according to [13], [15b], [16], and [24], respectively. Lipase PS from Pseudomonas cepacia (Amano Pharmaceuticals Co., Japan, 30 U mg À1 ) was employed in this work.…”

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confidence: 99%

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Natural p‐Menthene Monoterpenes: Synthesis of the Enantiomeric Forms of Wine Lactone, Epi‐wine Lactone, Dill Ether, and Epi‐dill Ether Starting from a Common Intermediate

Serra

Fuganti

2004

Helvetica Chimica Acta

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A concise synthesis of the enantiomeric forms of wine lactone (5), epi-wine lactone (14), dill ether (6), and epi-dill ether (15) was accomplished starting from the enantiomeric forms of p-mentha-1,8(10)-diene-3,9-diol (8) (Scheme 3). The latter compounds were previously prepared in high optical purity by means of lipasemediated kinetic resolution, and they were the common building blocks for this divergent synthesis. The key steps were a number of chemo-and diastereoselective reactions of which the oxidation of 8 to the lactone 7 (see Table 1), the diastereoselective reduction of 7 to the lactones 14 and 5 (see Table 2), and the reduction of enolether 16 to ether 15 were studied comprehensively. The effectiveness of this new synthetic approach allows the preparation of the title p-menthane monoterpenes, which are of considerable interest to the perfume industry, in high yield and in a few simple experimental steps.

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“…It has been found that a large number of substitution, elimination, addition, oxidation, and reduction reactions can be achieved by use of insoluble or polymer supported reagents ( I , 2). For example, recent publications have described the heterogeneous oxidation of organic compounds by chromyl chloride cheniisorbed on silica/alumina (3), pyridinium chlorochromate or dichromate on molecular sieve (4), chromium trioxide on graphite, Celite, or silica gel ( 3 , alumina or silica supported sodium metaperiodate (6), clay supported iron(ll1) nitrate (7), silver carbonate on Celite (8), polymer supported iodate. periodate, pyridinium dichroniate, or hypochlorite (9), and permanganate on a variety of solid supports including molecular sieve (101, alumina ( 1 I), silica ( 12), or bentonite ( 13).…”

Section: Introductionmentioning

confidence: 99%

Heterogeneous permanganate oxidations. 4. The oxidation of sulfides and selenides

Noureldin¹,

McConnell²,

Lee³

1984

Can. J. Chem.

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The heterogeneous oxidation of sulfides and selenides by copper(II) permanganate octahydrate or a mixture of potassium permanganate and copper(II) sulfate pentahydrate has been studied. Conditions under which quantitative conversions of the sulfides and selenides to the corresponding sulfones and selenones take place have been determined and an attempt has been made to visualize a mechanism for the reaction.

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Oxydations par le carbonate d'argent sur celite—XIII

Cited by 117 publications

References 24 publications

Stereochemistry of Formation of theβ-Ring of Lycopene: Biosynthesis of (1R,1′R)-β,β-[16,16,16,16′,16′,16′-2H6]Carotene from [16,16,16,16′,16′,16′-2H6]Lycopene inFlavobacterium R 1560

Stereochemistry of Formation of theβ-Ring of Lycopene: Biosynthesis of (1R,1′R)-β,β-[16,16,16,16′,16′,16′-2H6]Carotene from [16,16,16,16′,16′,16′-2H6]Lycopene inFlavobacterium R 1560

Natural p‐Menthene Monoterpenes: Synthesis of the Enantiomeric Forms of Wine Lactone, Epi‐wine Lactone, Dill Ether, and Epi‐dill Ether Starting from a Common Intermediate

Heterogeneous permanganate oxidations. 4. The oxidation of sulfides and selenides

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