Structure and Stereochemistry of Diels-Alder Adducts of Levopimaric Acid

Halbrook, Noah J.; Lawrence, Ray V.; Dressler, Robert L.; Blackstone, Robert C.; Herz, Werner

doi:10.1021/jo01028a008

Cited by 26 publications

(11 citation statements)

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“…and n.m.r. spectra (see Experimental) are consistent with the structure, and treatment of the isocyanate 5, prepared as described below, with concentrated sulfuric acid in chloroform gave compound 4. It thus appears that acid-catalyzed cyclization of the intermediate isocyanate (arrows in 5) occurs in preference to hydrolysis and decarboxylation under the conditions of the Schmidt reaction.…”

supporting

confidence: 60%

Rearrangements in the Diterpenoid Series. Part II. The Diazotization of Methyl 15-β-amino-13-isopropyl-17-noratis-13-en-18-oate

Ayer¹,

Deshpande²

1973

Can. J. Chem.

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Treatment of methyl 15-~-amino-l3-isopropyl-17-noratis-13-en-l8-0ate (10) with sodium nitrite -acetic acid gives rise to a variety of products, including nitrated compounds and norketones. The structures of seven of the products have been established. The reaction of methyl 16-isopropylidene-7,l7-secoacon-8(15)-en-18-oate (2) with nitrous acid and with dinitrogen tetroxide is described. A simple method for transforming isocyanates to primary amines is presented.La reaction du methylamino-a-15 isopropyl-13 noratis-17 h e -1 3 oate-18 (lb) avec de l'acide acetiquenitrite de sodium donne lieu a plusieurs produits parmi lesquels on trouve des cornposCs nitres et des norcetones. Les structures de sept de ces produits ont CtC ClucidCes. La reaction du rnkthyl isopropylidene-16 secoacon-7.17 he-8(15) oate-18 (2) avec de I'acide nitreux et du tetroxyde de diazote est decrite. Une methode simple pour la transformation des isocyanates en amines primaires est decrite.[Traduit par le journal]Can.

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supporting

confidence: 60%

Rearrangements in the Diterpenoid Series. Part II. The Diazotization of Methyl 15-β-amino-13-isopropyl-17-noratis-13-en-18-oate

Ayer¹,

Deshpande²

1973

Can. J. Chem.

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“…Thus we decided to follow the literature suggestion 11 to carry out the ozonolysis of 1 at 0 o C in CH 2 Cl 2 solution in the presence of tetracyanoethylene (TCNE) in attempt to minimize the formation of the undesired products obtained previously by Zalkow 4,6,7 and Halbrook 8 . Although in this case the mechanism is not clear, the catalytic action of TCNE on the alcoholysis of epoxides is well known due to its π-acid and one-electron acceptor properties 12 .…”

Section: Resultsmentioning

confidence: 99%

Synthetic studies with Pinus elliottiis rosin derivatives. Oxidation of maleopimaric anhydride methyl ester and trimethyl fumaropimarate

Hess

Farah

Eguchib

et al. 2000

J. Braz. Chem. Soc.

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A ozonólise do éster metílico do anidrido maleopimárico na presença de tetracianoetileno produziu um epóxido e um ozonídeo, e a ozonólise do fumaropimarato de trimetila, seguida por tratamento com Me 2 S, forneceu um epóxido, um dieno, um ceto-ácido e um produto de oxidação alílica. Alguns dos compostos obtidos apresentaram atividade antibacteriana contra Staphylococcus aureus, Bacilllus subtilis e Micrococcus luteus.Ozonolysis of maleopimaric anhydride methyl ester in the presence of tetracyanoethylene led to an epoxide and an ozonide. Ozonolysis of the trimethyl fumaropimarate, followed by treatment with Me 2 S, led to an epoxide, a diene, a keto-acid and an allylic oxidation product. Some of the compounds obtained were active against Staphylococcus aureus, Bacillus subtilis and Micrococcus luteus.

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“…111 order to confirm the position and orientatioil of the acetyl group the adduct was treated with sodiurn hypobromite. After the crude product of this reaction was esterified wit11 diazomethane and subjected to chromatography over alu~nina the isopropylidene lactone 9 of known constitution (3,7,8) was obtained in 11% yield, establishing that the acetyl group is located at C-15 and supporting the endo assignment of configuration.…”

Section: Traduit Par Le Journal]mentioning

confidence: 76%

Rearrangements in the Diterpenoid Series. I. The Solvolysis of Methyl 15β-tosyloxy-13-isopropyl-17-noratis-13-en-18-oate

Ayer¹,

Deshpande²

1973

Can. J. Chem.

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Structure and Stereochemistry of Diels-Alder Adducts of Levopimaric Acid

Cited by 26 publications

References 0 publications

Rearrangements in the Diterpenoid Series. Part II. The Diazotization of Methyl 15-β-amino-13-isopropyl-17-noratis-13-en-18-oate

Rearrangements in the Diterpenoid Series. Part II. The Diazotization of Methyl 15-β-amino-13-isopropyl-17-noratis-13-en-18-oate

Synthetic studies with Pinus elliottiis rosin derivatives. Oxidation of maleopimaric anhydride methyl ester and trimethyl fumaropimarate

Rearrangements in the Diterpenoid Series. I. The Solvolysis of Methyl 15β-tosyloxy-13-isopropyl-17-noratis-13-en-18-oate

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