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    • 3. 发明专利
    • Synthesis of optically active (-)-oudemansin
    • 光学活性( - ) - OUDEMANSIN的合成
    • JPS59163348A
    • 1984-09-14
    • JP3692983
    • 1983-03-07
    • Rikagaku Kenkyusho
    • OOISHI TAKESHIHORIKOSHI KOUKIAKITA HIROYUKIKOSHIJI HIROKOFURUICHI AKINARI
    • C12P7/62C07C67/00C07C69/734C12R1/72
    • PURPOSE:To prepare the titled compound useful as an antibacterial agent, by reducing a beta-ketoester with a microorganism belonging to Candida genus, and subjecting the resultant beta-hydroxyester to the reaction of several steps. CONSTITUTION:The compound of formula I is reduced to the compound of formula II with microorganism belonging to Candida genus (e.g. Candida albicans), and the product is reduced with LiAlH4 to obtain the compound of formula III(R is H). The product is t-butyldimethylsilylated (SiMe2Bn), and treated with methyl iodide to obtain the compound of formula IV (R is SiMe2Bn). After eliminating the t-butyldimethylsilyl group from the compound, the compound is treated with p-toluenesulfonic acid chloride then with a cyanide, hydrolyzed, methylated with diazomethane, formylated with lithium diisopropylamide and methyl formate, treated with an alkali and finally treated with diazomethane to obtain the objective compound of formula V.
    • 目的:制备用作抗菌剂的标题化合物,通过用属于念珠菌属的微生物还原β-酮酯,并使得到的β-羟基酯进行几个步骤的反应。 构成:将式I化合物用属于念珠菌属(例如白色假丝酵母属)的微生物还原成式II化合物,用LiAlH 4还原产物,得到式Ⅲ化合物(R为H)。 产物为叔丁基二甲基甲硅烷基化(SiMe2Bn),用碘甲烷处理得到式Ⅳ化合物(R为SiMe 2 Bn)。 在从化合物中除去叔丁基二甲基甲硅烷基后,化合物用对甲苯磺酰氯处理,然后用氰化物处理,水解,用重氮甲烷甲基化,用二异丙基氨基锂和甲酸甲酯甲酰化,用碱处理,最后用重氮甲烷处理 得到式Ⅴ的目的化合物。
    • 10. 发明专利
    • PREPARATION OF DITERPENE DERIVATIVE COMPOUND
    • JPS58113146A
    • 1983-07-05
    • JP22910782
    • 1982-12-27
    • RIKAGAKU KENKYUSHO
    • AKITA HIROYUKI
    • C07C69/716C07C67/00C07C69/757
    • PURPOSE:To obtain the titled compound useful as an intermediate for synthesizing a physiologically active substance, by oxidizing a specific diterpene phenol derivative as a raw material with ozone so that an aromatic ring is subjected to cleavage, reducing catalytically the resultant compound, followed by methylating the reduced compound with diazomethane. CONSTITUTION:A deterpene phenol derivative shown by the formula II (R is CH3 or methoxycarbonyl) obtained easily form an l-abietic acid shown by the formulaI, a main component of a resin of a conifer, is oxidized with extremely excess O3 at -80-0 deg.C in a solvent, reduced catalytically using a catalytically reducing agent such as 10% Pd-C, etc. or zinc-acetic acid at 0-30 deg.C for 30min- 12hr, and methylated with a diazomethane-ether solution, to give the desired compound such as 8-oxo-(13 17)-pentanorlabdan-12-oic acid methyl ester (a novel substance wherein R is CH3) shown by the formula III. USE:An intermediate for synthesizing dimethyl sciadinonate showing growth inhibiting action on larvae of cocoon.