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Bicyclo hexane-6-carboxylic acid

Yoshikawa, N., Tan, L., Yasuda, N., et al. (2004) Enantioselective syntheses of bicyclo[3.1.0]hexane carboxylic acid derivatives by intramolecular cyclopropanation. Tetrahedron Letters, 45, 7261-7264. [Pg.97]

A few natural products which contain the cyclopropyl ring have been synthesized through metal catalysed cyclopropanation using dicarbonyl diazomethanes. ( )-Cycloeudesmol 63, isolated from marine alga Chondria oppositiclada, was synthesized via a sequence involving a copper catalysed cyclopropanation of a-diazo-/8-ketoester 61 to give the key intermediate 62 (equation 73)1 7,108. Similarly, the bicyclo[3.1.0]hexane derivative 65 was synthesized from the corresponding a-diazo-/8-ketoester 64 via the catalytic method and was converted into ( )-trinoranastreptene 66 (equation 74)109. Intramolecular cyclopropanation of -diazo-/i-ketoesters 67 results in lactones 68 which are precursors to 1-aminocyclopropane-l-carboxylic acids 69 (equation 75)110. [Pg.677]

To a solution of 5-hydroxy-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester (4 g, 23.5 mmol) in CH2CI2 (100 ml) was added N,N -diisopropylethylamine (12.3 ml, 70.5 mmol) followed by chloromethyl methyl ether (3.6 ml, 47 mmol, distilled from tech, grade). The solution was refluxed for 3.5 h and the solvent was evaporated. The residue was partitioned between ethyl acetate (200 ml) and water (200 ml). The aqueous phase was extracted with ethyl acetate (100 ml). The combined organic extracts were washed with saturated NaCI (100 ml), dried (MgS04), filtered, and evaporated to afford 4.9 g of a solid residue of 5-methoxymethoxy-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester which was of suitable purity to use directly in the next step melting point 62°-65°C (crude) melting point 64°-66°C (diethyl ether/hexane). [Pg.2525]

On the other hand, cation formation by decarboxylation of an acyloxonium cation RC02+ is supported by the partial stereospecificity observed in the electrolysis of cis- and trans-bicyclo [3.1.0] hexane-3-carboxylic acid 2°5 and the electrocyclic ring opening in the anodic oxidation of 3-methyl-2-phenylcyclopro-panecarboxylate (22, 23) to cyclopropyl methyl ether (24, 25) and allylic ethers (26, 27) (Eq. (97)) 206). [Pg.64]

The electrolytic decarboxylations of either cis- or trari5-bicyclo[3.1.0]hexane-3-carboxylic acids (74), gave the same products although in different ratios. The... [Pg.952]

Bicyclo[2.2.0]hexa-Sacid anhydride, 556 Bicyclo(2.1.1]hexane, 89 -5-carboxylic acid, 89 cu-Bicydo[3.I.O]hexanol, 1021 l,r-Bicyclohexenyl, 182 Bicyclohexylidene, 1021 Bicyclo[4.2.0]acta-2,4-diene-7,8-diol diacetate, 183-184... [Pg.700]

Decarboxylation. Wiberg and co-workers developed an interesting method for decarboxylating bicyclo[2.1.1]hexane-5-carboxylic acid (1) to the parent hydrocarbon (4). The acid chloride (2) was stirred into a mixture of f-butyl hydroperoxide... [Pg.778]

Fig. 11.6 Structures of bridged bicyclic proline mimetics (22) 2-aza-bicyclo[2.2.1]hep-tane-3-carboxylic acid, (23) 2-aza-bicy-clo[2.2.1]hept-5-ene-3-carboxylic acid, (24) 7-aza-bicyclo[2.2.1]heptane-l-carboxylic acid, (25) 2-aza-bicyclo[2.2.1]hexane-l carboxylic acid, (26) 2-aza-bicyclo[2.2.1]hexane-... Fig. 11.6 Structures of bridged bicyclic proline mimetics (22) 2-aza-bicyclo[2.2.1]hep-tane-3-carboxylic acid, (23) 2-aza-bicy-clo[2.2.1]hept-5-ene-3-carboxylic acid, (24) 7-aza-bicyclo[2.2.1]heptane-l-carboxylic acid, (25) 2-aza-bicyclo[2.2.1]hexane-l carboxylic acid, (26) 2-aza-bicyclo[2.2.1]hexane-...
Besides the obvious D3 twisted bicyclo[2.2.2]octane framework, another characteristic of pentacyclic [m.n.o] triblattanes is the presence of a strained bicyclo [2.2.0] hexane moiety whose facile reductive cleavage of the central single bond correlates this class of triblattanes to the corresponding tetracyclic [m.n] triblattanes. Figure 21 illustrates the configurational correlation between these two classes of triblattanes the key liaison compound is the (+) <, 0-unsaturated ketone 172, whose absolute configuration had been related to that of the levorotatory carboxylic acid (-)-151 via (+)-methyl 3-(enrfo-2-norbornyl) propionate (179) (146). [Pg.232]

Sodium hydroxide Scherer ring contraction Bicyclo[2.2.0]hexane-l-carboxylic acids... [Pg.57]

Ring contraction. A soln. of 3-diazonopinone in dioxane-water irradiated 190 hrs. in a Pyrex vessel with 15-w. Sylvania Blacklite tubes 5,5-dimethyl-bicyclo[2.1.1]hexane-2j -carboxylic acid. Y 68%. J. Meinwald and P. G. Gass-man, Am. Soc. 82, 2857 (1960). [Pg.440]

During oxidation of bicyclo-[0,l,3]-hexane-3-carboxylic acid in a mixture of pyridine and water (1 3) Gassmann and Zalar [95] obtained not the 3-substituted but the 2-substituted alcohol as major product (with a yield of 70-80%). The cis- and trans-isomeric acids give mainly the cis- and trans-alcohols respectively thus, the cis acid ... [Pg.157]

Bicyclo [2.1.1] hexane-5-carbonyl chloride added during 1 hr. with ice-saltcooling to a stirred mixture of ferf-butyl hydroperoxide, dry pyridine and p-cymene, stirring and cooling continued for an additional hr., poured onto ice, the p-cymene phase containing ferf-butyl bicyclo [2.1.1] hexane-5-peroxy-carboxylate separated, washed, dried, and heated in a wax bath at 115-130 until GOg-evolution ceases after 2 hrs., then distilled until the head temp, reaches 176° (p-cymene) bicyclo [2.1.1] hexane. Y 45%.—This is a convenient method for the decarboxylation of aliphatic acids. F. e. with lower yield s. K. B. Wiberg, B. R. Lowry, and T. H. Golby, Am. Soc. 83, 3998 (1961). [Pg.332]


See other pages where Bicyclo hexane-6-carboxylic acid is mentioned: [Pg.2527]    [Pg.2527]    [Pg.453]    [Pg.903]    [Pg.68]    [Pg.564]    [Pg.276]    [Pg.1273]    [Pg.236]    [Pg.260]    [Pg.2312]    [Pg.243]    [Pg.310]    [Pg.675]    [Pg.276]    [Pg.409]   


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