A synthesis of 2-aminonorbornene-2-carboxylic acid derivatives by diels-alder reaction using α,β-dehydroalaninates as a dienophile

Horikawa, Hiroshi; Noji, Takashi; Iwasaki, Tameo; Mushika, Yoshitaka; Inoue, Ichizo; Miyoshi, Muneji

doi:10.1016/0040-4039(80)88077-4

Cited by 46 publications

(5 citation statements)

References 10 publications

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“…Tager and Christensen 1972; Cativiela et al. 1990) the differentiation of the isomers has been based on the shielding effect of the double bond in olefinic precursors (Horikawa et al. 1980) and, to our knowledge, only a subset of 1 H chemical shifts for BCH has been reported.…”

Section: Methodsmentioning

confidence: 99%

Alanine metabolism, transport, and cycling in the brain

Bröer¹,

Bröer²,

Hansen³

et al. 2007

Journal of Neurochemistry

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Brain glutamate/glutamine cycling is incomplete without return of ammonia to glial cells. Previous studies suggest that alanine is an important carrier for ammonia transfer. In this study, we investigated alanine transport and metabolism in Guinea pig brain cortical tissue slices and prisms, in primary cultures of neurons and astrocytes, and in synaptosomes. Alanine uptake into astrocytes was largely mediated by system L isoform LAT2, whereas alanine uptake into neurons was mediated by Na(+)-dependent transporters with properties similar to system B(0) isoform B(0)AT2. To investigate the role of alanine transport in metabolism, its uptake was inhibited in cortical tissue slices under depolarizing conditions using the system L transport inhibitors 2-aminobicyclo[2.2.1]heptane-2-carboxylic acid and cycloleucine (1-aminocyclopentanecarboxylic acid; cLeu). The results indicated that alanine cycling occurs subsequent to glutamate/glutamine cycling and that a significant proportion of cycling occurs via amino acid transport system L. Our results show that system L isoform LAT2 is critical for alanine uptake into astrocytes. However, alanine does not provide any significant carbon for energy or neurotransmitter metabolism under the conditions studied.

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Section: Methodsmentioning

confidence: 99%

Alanine metabolism, transport, and cycling in the brain

Bröer¹,

Bröer²,

Hansen³

et al. 2007

Journal of Neurochemistry

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“…It is worth noting that these results differ from those of the reaction of α,β‐dehydroalanine derivatives with cyclopentadiene, where the observed exo/endo ratios depend on the nature and the steric hindrance of the N ‐acyl and ester groups. Moreover, they are generally lower than those observed for the corresponding 1‐aminovinylphosphonate esters …”

Section: Resultsmentioning

confidence: 59%

1‐Aminovinylphosphonate Esters as Substrates for the Diels‐Alder Reaction: First Synthetic and Theoretical Study

et al. 2019

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The Diels‐Alder reaction of 1‐aminovinylphosphonate esters has been studied for the first time as a suitable procedure leading to quaternary carbocyclic α‐aminophosphonates. The reaction is influenced by steric effects at the phosphonate functionality (bulky groups hinder the reaction) and electronic effects at the amino group (electron‐withdrawing substituents increase the reaction rate). The exo/endo ratio is constant, and no influence of the solvent is observed. The experimental results have been rationalized by DFT methods.

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“…The Diels-Alder reaction of a,b-dehydroalanine derivatives with 1,3-butadiene was first investigated by Horikawa in 1980. 129 The acylated ester yielded, at 90°C in toluene, or at room temperature in CCl 4 with AlCl 3 or FeCl 3 in ether, 62-79% of a mixture of the exo and endo product (60:40). The methoxycarbonyl-protected ester gave exclusively the exo product in 56% yield.…”

Section: Diels-alder Reactionsmentioning

confidence: 99%

α,β-Dehydroamino Acids

Bonauer¹,

Walenzyk²,

König³

2006

Synthesis

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a,b-Dehydroamino Acids a , b -D e h y d r o a m i n o A c i d sAbstract: Dehydroamino acids are versatile intermediates in organic synthesis and occur as frequent structural motives in natural products and biologically active compounds. This review summarizes recent work (since 1999) on the synthesis, reactions and applications of acyclic and cyclic a,b-dehydroamino acids, a,bdehydroamino esters, and protected a,b-dehydroamino acids. 6Conclusions

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A synthesis of 2-aminonorbornene-2-carboxylic acid derivatives by diels-alder reaction using α,β-dehydroalaninates as a dienophile

Cited by 46 publications

References 10 publications

Alanine metabolism, transport, and cycling in the brain

Alanine metabolism, transport, and cycling in the brain

1‐Aminovinylphosphonate Esters as Substrates for the Diels‐Alder Reaction: First Synthetic and Theoretical Study

α,β-Dehydroamino Acids

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