Prostaglandins. X. Synthesis of prostaglandin models and prostaglandins by conjugage addition of a functionalized organocopper reagent

Abstract

A solution of 500 mg of (±)-11-deoxyprostaglandin Ei was dissolved in 30 ml of methanol and solid sodium borohydride was added portionwise until no more starting material could be detected by tic analysis (40% ethyl acetate-60% hexane). The reaction solution was poured into water and extracted with ethyl acetate. The organic phase was washed with brine and dried over anhydrous sodium sulfate. The solvent was eliminated under reduced pressure and the residue purified via preparative tic to yield 303 mg of (±)-11-deoxyprostaglandin Fia methyl ester and 98 mg of its 9/3 epimer. Basic hydrolysis of these compounds in the usual manner yielded (±)-ll-deoxyprostaglandin Fia [mp 97-98.5°; ir 3400 (br), 3160 (br), 2970 (sh), 2930 (s), 2860 (sh), 1695 (s), 9.75 (s) cm'1; nmr 2.31 (t, / = 7 Hz, CH,CO), 4.00-4.30 (m, 2 H, CHOH), 5.

Recent developments in use of heteropolyacids, their salts and polyoxometalates in organic synthesis

“…and are readily removed by mild acid treatment. The commonly employed methods for the preparation of methoxymethyl ethers is based on the reaction of the corresponding alkoxide anions with chloromethyl methyl ether (MOM-Cl) [108].…”

Synthesis and characterization of phosphorous-bridged bisphenoxy titanium complexes and their application to ethylene polymerization

“…2-tert-Butyl-1-(methoxymethoxy)-4-methylbenze (1) [21] and dichloro-(pentafluorophenyl)phosphine [22] were synthesized by published methods. Dichloro(2-dimethylaminomethylphenyl)phosphine was prepared by the reaction of phosphorus trichloride and the lithium salt of N,N-dimethylbenzylamine [23].…”

One-Pot Synthesis of 5-Aryl Diketo-1H-tetrazol Using 1-Methyl-1-methoxyethyl as Protective Group

“…醇羟基与二甲氧基丙烯在催化量质子酸的条件 下反应生成 MME 醚, 而脱保护仅需 20%醋酸水溶液即 可脱除 [9] . 该类保护基对碱性反应体系稳定, 保护与脱 保护条件温和, 所以我们尝试以 MME 作为保护基用于 芳香二酮四氮唑类化合物的合成.…”