Hydroboration-Oxidation of (+/-)-(1,3,3a,6a)-1,2,3,3a,4,6a-Hexahydro-1,3-pentalenedimethanol and Its O-Protected Derivatives: Synthesis of New Compounds Useful for Obtaining (iso)Carbacyclin Analogues and X-ray Analysis of the Products

Tanase Constantin I.; Cocu Florea G.; Caproiu Miron Teodor; Draghici Constantin; Shova Sergiu

首页> 外文期刊>Molecules >Hydroboration-Oxidation of (+/-)-(1,3,3a,6a)-1,2,3,3a,4,6a-Hexahydro-1,3-pentalenedimethanol and Its O-Protected Derivatives: Synthesis of New Compounds Useful for Obtaining (iso)Carbacyclin Analogues and X-ray Analysis of the Products

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Hydroboration-Oxidation of (+/-)-(1,3,3a,6a)-1,2,3,3a,4,6a-Hexahydro-1,3-pentalenedimethanol and Its O-Protected Derivatives: Synthesis of New Compounds Useful for Obtaining (iso)Carbacyclin Analogues and X-ray Analysis of the Products

机译：（+/-） - （1,3,3a，6a）-1,2,3,3a，4,6a-六羟基甲醇及其o保护衍生物的氧化氧化 - （1,3,3a，6a）-1,2,3,3a，4,6a-六羟基甲醇及其O-保护衍生物：新化合物的合成可用于获得（ISO）Carbacyclin类似物和产品的X射线分析

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Hydroboration-oxidation of 2,4-dimethanol-1,5-bicyclo[3.3.0]oct-6-en dibenzoate (1) gave alcohols 2 (symmetric) and 3 (unsymmetric) in similar to 60% yield, together with the monobenzoate diol 4a (37%), resulting from the reduction of the closer benzoate by the intermediate alkylborane. The corresponding alkene and dialdehyde gave only the triols 8 and 9 in similar to 1:1 ratio. By increasing the reaction time and the temperature, the isomerization of alkylboranes favours the un-symmetrical triol 9. The PDC oxidation of the alcohols gave cleanly the corresponding ketones 5 and 6 and the deprotection of the benzoate groups gave the symmetrical ketone 14, and the cyclic hemiketal 15, all in high yields. The ethylene ketals of the symmetrical ketones 11 and 13 were also obtained. The compounds 5, 6, 11, 13, 14 could be used for synthesis of new (iso)carbacyclin analogues. The structure of the compounds was established by NMR spectroscopy and confirmed by X-ray crystallography.

机译：2,4-二甲醇-1,5-双环[3.3.0] 10℃-6-烯二苯甲酸盐（1）的水合氧化氢-6-烯苯甲酸盐（1）得到醇2（对称）和3（非对称），类似于60％的产率，以及单苯甲酸二醇4a（37％），由中间烷基硼烷的近苯甲酸酯的减少引起。相应的烯烃和二醛仅在类似于1：1的比例中产生三醇8和9。通过增加反应时间和温度，烷基硼烷物的异构化伴随着不对称的三醇9。醇的PDC氧化干净地给出了相应的酮5和6，苯甲酸酯基团的脱保护给出了对称的酮14，以及循环长臂15，均高产。还得到了对称酮11和13的乙烯酮。化合物5,6,11,13,14可用于合成新的（ISO）碳酸类类似物。通过NMR光谱建立化合物的结构，并通过X射线晶体学证实。

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来源
《Molecules》 |2017年第12期|共18页
作者
Tanase Constantin I.; Cocu Florea G.; Caproiu Miron Teodor; Draghici Constantin; Shova Sergiu;
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作者单位

Natl Inst Chem Pharmaceut Res &

Dev Dept Bioact Subst &

Pharmaceut Technol 112 Vitan Ave Bucharest 031299 3 Romania;

Natl Inst Chem Pharmaceut Res &

Dev Dept Bioact Subst &

Pharmaceut Technol 112 Vitan Ave Bucharest 031299 3 Romania;

Organ Chem Ctr CD Nenitescu Spect Lab 202 B Splaiul Independentei Bucharest 060023 Romania;

Organ Chem Ctr CD Nenitescu Spect Lab 202 B Splaiul Independentei Bucharest 060023 Romania;

Inst Macromol Chem Petru Poni Dept Crystallog Iasi 700478 Romania;

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原文格式 PDF
正文语种 eng
中图分类有机化学;
关键词
hydroboration-oxidation; borane; sodium acetoxyborohydride; hexahydro-1; 3-pentalenedimethanol; octahydropentalene-triols; octahydropentalene-ketones; X-ray analysis;

机译：氢化氢;硼烷;乙酰氧基硼氢化钠;六碳二甲醇;3-普利替替二甲醇;八氢丁烯 - 三醇;八氢香脂;X射线分析;

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1. Hydroboration-Oxidation of (+/-)-(1,3,3a,6a)-1,2,3,3a,4,6a-Hexahydro-1,3-pentalenedimethanol and Its O-Protected Derivatives: Synthesis of New Compounds Useful for Obtaining (iso)Carbacyclin Analogues and X-ray Analysis of the Products [J] . Tanase Constantin I., Cocu Florea G., Caproiu Miron Teodor, Molecules . 2017,第12期

机译：（+/-） - （1,3,3a，6a）-1,2,3,3a，4,6a-六羟基甲醇及其o保护衍生物的氧化氧化 - （1,3,3a，6a）-1,2,3,3a，4,6a-六羟基甲醇及其O-保护衍生物：新化合物的合成可用于获得（ISO）Carbacyclin类似物和产品的X射线分析
2. MCPB treatment of (+/-)-(1 alpha,3 alpha,3a beta,6a beta)-1,2,3,3a,4,6a-hexahydro-1,3-pentalenedimethanol and its O-acyl-protected derivatives; X-ray crystallography [J] . Tanase Constantin I., Draghici Constantin, Caproiu Miron Teodor, Tetrahedron . 2015,第24期

机译：MCPB处理（+/-）-（1 alpha，3 alpha，3a beta，6a beta）-1,2,3,3a，4,6a-六氢-1,3-五烯二甲醇及其O-酰基保护的衍生物; X射线晶体学
3. 1,2,3,3a,4,6a-hexahydro-1,3-pentalenedimethanol,mono And Bis Oh-protected Derivatives, Useful Intermediates For Fine Organic Synthesis [J] . Constantin I. TANASE, Florea G. COCU, Constantin DRAGHICI, Revue roumaine de chimie . 2008,第3期

机译：1,2,3,3a，4,6a-六氢-1,3-五烯二甲醇，单和双OH保护的衍生物，适用于精细有机合成的中间体
4. Hydroboration-Oxidation of (±)-(1α,3α,3aβ,6aβ) -1,2,3,3a,4,6a-Hexahydro-1,3-pentalenedimethanol and Its O-Protected Derivatives: Synthesis of New Compounds Useful for Obtaining (iso)Carbacyclin Analogues and X-ray Analysis of the Products [O] . Constantin I. Tănase, Florea G. Cocu, Miron Teodor Căproiu, 2017

机译：（±） - （1α，3α，3aβ，6aβ）-1,2,3,3a，4,6a-六氢-1,3-戊二醇二甲醇的氢化 - 氧化其O-保护衍生物：合成可用于获得（iso）Carbacyclin类似物的新化合物和产品的X射线分析

Hydroboration-Oxidation of (+/-)-(1,3,3a,6a)-1,2,3,3a,4,6a-Hexahydro-1,3-pentalenedimethanol and Its O-Protected Derivatives: Synthesis of New Compounds Useful for Obtaining (iso)Carbacyclin Analogues and X-ray Analysis of the Products

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