Total synthesis of the macrolide antibiotic (±)-A26771B

Asaoka, Morio; Yanagida, Noboru; Takei, Hisashi

doi:10.1016/0040-4039(80)80087-6

Cited by 46 publications

(16 citation statements)

References 6 publications

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“…An alternate esterification procedure, described by Kataoka et al, 7 used the tri-n-butylammonium salt of cAMP, benzyl bromide, and sodium carbonate in dimethylacetamide. When applied to esterification of cAMP with the substituted benzyl bromide 8, these conditions successfully gave a mixture of 10a and its equatorial isomer 11a (∼3:1 ratio) in overall 25-30% yield.…”

Section: Resultsmentioning

confidence: 99%

“…The filtrate was washed with 1 M NaHSO4 (100 mL), saturated NaHCO3 (60 mL), and H2O (60 mL), dried, and evaporated. Flash chromatography (98:2 CH2-Cl2-EtOAc) gave 6 as an oil (0.917 g, 90%): 1 H NMR δ 4.13-4.32 (m, 4H), 4.08 (s, 2H), 3.98 (s, 2H), 1.44 (s, 9H), 0.90-1.09 (7). A solution of 4 M HCl in anhydrous dioxane (7 mL) was added to 6 (0.34 g, 0.78 mmol), and the mixture was stirred at room temperature for 1 h. The solvent was evaporated, and the residue was dissolved in water (60 mL).…”

Section: N-boc-iminodiacetic Acid Bis[2-(trimethylsilyl)ethyl] Ester (6)mentioning

confidence: 99%

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Photolabile Precursors of Cyclic Nucleotides with High Aqueous Solubility and Stability

2002

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Photolabile phosphotriester derivatives of cyclic AMP and cyclic GMP are described, where the additional group on the phosphate is a 2-nitrobenzyl that bears an electron-withdrawing and dianionic substituent. This confers high aqueous solubility and excellent resistance to hydrolysis of the phosphotriester (t(1/2) for hydrolysis at pH 7, 22 degrees C, is >3 months for the axial isomers 3a and 4a and >1 month for the equatorial isomers 3b and 4b). The photolysis quantum yields are in the range 0.15-0.24, and the product release rate upon flash photolysis is 1.7 s(-1) at pH 7.0, 20 degrees C.

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Section: Resultsmentioning

confidence: 99%

Section: N-boc-iminodiacetic Acid Bis[2-(trimethylsilyl)ethyl] Ester (6)mentioning

confidence: 99%

Photolabile Precursors of Cyclic Nucleotides with High Aqueous Solubility and Stability

2002

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“…In this manner, lactone 66 was formed in 48% yield along with its corresponding dimers, trimers, and tetramers, as well as neopentyl alcohol (55) and DMF (5) (Scheme 15). 75 This new lactonization procedure has subsequently found a number of applications [76][77][78][79][80][81][82][83][84] giving lactones in yields of up to 90%. Analogously, ether formation from the reaction of phenols 16 with chiral alcohols 2 in the presence of DMF dineopentyl acetal 7d affords, via phenolate anions 17, the corresponding inverted phenyl ethers 18.…”

Section: Scheme 11mentioning

confidence: 99%

Section: Scheme 11mentioning

confidence: 99%

Esterification of Carboxylic Acids and Etherification of Phenols with Amide Acetals

Vorbrüggen¹

2008

Synlett

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The esterification and etherification of unhindered, as well as severely hindered, carboxylic acids and phenols with basic amide acetals, such as N,N-dimethylformamide dimethyl acetal, and their side reactions are discussed. Modified procedures are described in which these side reactions are avoided to achieve high or near quantitative yields of the desired corresponding methyl esters or phenol methyl ethers. On the addition of N,N-dimethylformamide dimethyl acetal, solutions of 4-nitrobenzoic acid in basic solvents, such as tetrahydrofuran or 1,4-dioxane, form precipitates of the corresponding iminium carboxylates, which give near quantitative yields of the desired methyl 4-nitrobenzoate, as well as N,Ndimethylformamide and methanol.

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“…57 The synthesis begins with the addition of methyl lithium to 10-undecenal (24) and acetylation of the resulting alcohol to give 25 in 98% yield. A hydroboration-oxidation sequence gave the primary alcohol, which was further oxidized to aldehyde 26 (70%).…”

Section: A A26771bmentioning

confidence: 99%