Total syntheses of (±) aminoallose derivatives

Defoin, Albert; Fritz, Hans; Geffroy, Guillaume; Streith, Jacques

doi:10.1016/s0040-4039(00)85049-2

Cited by 19 publications

(12 citation statements)

References 9 publications

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“…This hybridization produces i) a strong anomeric effect which forces the OH-C(l) substituent to be axial (vide supra) and ii) a strong steric effect which would be manifest in the alternative 'C,(D) chair conformation because of the severe steric repulsion between the equatorial Me-C(5) substituent and the N-acyl group. Therefore, we believe that both the anomeric effect and the steric effect act together in favour of the 'C'(D) conformation of 17c and 17f (see Scheme 3). Similar steric features have been observed with P-D-xylopyranoses [26] [27] as well as with u -D-idopyranoses [24] [25] [28].…”

Section: Hsupporting

confidence: 63%

“…This was demonstrated for 7c and 8c as follows: irradiation of Me at 16-17 ppm leads to a simple t which is analogous to the ones described above. Thus, the C-atom bearing the Me group is connected to N(2) and identified as C (3). Clearly, in all adducts 7 and 8 the ring 0-atoms appear on the side of the acetal moiety, demonstrating thereby the same regiospecificity of all cycloaddition reactions.…”

Section: 1mentioning

confidence: 88%

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Syntheses of Amino‐dideoxyallose and Amino‐deoxyribose Derivatives Using Acylnitroso Dienophiles

Defoin

Fritz

Geffroy

et al. 1988

Helvetica Chimica Acta

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Dedicated to Professor Elius J. Corey on the occasion of his 60th birthday (26.V11.88)The dimethyl acetals 4 of (E)-2,4-pentadienal and of (E,E)-and (E,Z)-2,4-hexadienals undergo regio-and stereospecific cycloaddition reactions with in-situ-generated acylnitroso dienophiles Sa and Sb, leading thereby to the corresponding dihydrooxazines 7a-d and 8c-d. cis-Glycolization of these latter adducts stereospecifically gave the dihydro derivatives 9a-d and 10d which, after sequential hydrogenolysis, deacetalization, and instant cyclization, led to the aminodeoxyribose derivatives 17a, 17f, and 18, and to the amino-dideoxyallose compounds 17c and 17b. These piperidino-deoxysugar derivatives exhibit a strong anomeric effect, i.e. OH-C( 1) is always axial, which is explained in terms of a n,(n)-o*(C-OH) orbital compression, as compared to the less pronounced one in the more classical pyranose series.

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Section: Hsupporting

confidence: 63%

Section: 1mentioning

confidence: 88%

Syntheses of Amino‐dideoxyallose and Amino‐deoxyribose Derivatives Using Acylnitroso Dienophiles

Defoin

Fritz

Geffroy

et al. 1988

Helvetica Chimica Acta

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“…A Swiss group in Basel used very similar methodology for a one-pot synthesis of the tricyclic mitomycin skeleton. [257] A hetero–Diels-Alder between nitrosobenzene and pentadienal gave an intermediate which proceeded through an analogous hetero-Cope rearrangement to give a hydroxypyrroloindole.…”

Section: The Mitomycins: Synthetic Studiesmentioning

confidence: 99%

Mitomycinoid Alkaloids: Mechanism of Action, Biosynthesis, Total Syntheses, and Synthetic Approaches

et al. 2013

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“…The HDA cycloaddition proceeds regio- and stereospecifically leading to the expected dihydrooxazine 71 in 61% yield (Scheme ). , …”

Section: Nitrosocarbonyl Generation Methodsmentioning

confidence: 99%

Generation and Trapping of Nitrosocarbonyl Intermediates

Memeo

Quadrelli

2017

Chem. Rev.

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The nitrosocarbonyls (R-CONO) are highly reactive species and remarkable intermediates toward different synthetic targets. This review will cover a research area whose impact in current organic synthesis is constantly increasing in the chemical community. This review represents the first and comprehensive picture on the generation and trapping of nitrosocarbonyls and is solidly built on more than 380 papers. Six different classes of key starting materials such as hydroxamic acids, N-hydroxy carbamates, N-hydroxyureas, nitrile oxides, and 1,2,4-oxadiazole-4-oxides were highlighted. The content of the review surveys all the methods to generate the nitrosocarbonyls through different approaches (oxidative, thermal, photochemical, catalytic, aerobic, and the less common ones) in the light of efficiency, yields, and mildness. The most successful trapping agents employed to catch these fleeting intermediates are reviewed, exploiting their superior dienophilic, enophilic, and electrophilic power. The work is completed by paragraphs dedicated to the detection of the intermediates, theoretical studies, and insights about the challenges and future directions for the field.

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Total syntheses of (±) aminoallose derivatives

Cited by 19 publications

References 9 publications

Syntheses of Amino‐dideoxyallose and Amino‐deoxyribose Derivatives Using Acylnitroso Dienophiles

Syntheses of Amino‐dideoxyallose and Amino‐deoxyribose Derivatives Using Acylnitroso Dienophiles

Mitomycinoid Alkaloids: Mechanism of Action, Biosynthesis, Total Syntheses, and Synthetic Approaches

Generation and Trapping of Nitrosocarbonyl Intermediates

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