从莽草酸出发合成井冈霉醇胺和一些手性环氧中间体以及氯化铜促进的肟与腙再生成醛酮的方法研究
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摘要
本文由下面三部分构成：
(1)第一部分描述了从莽草酸出发合成糖苷酶抑制剂井冈霉醇胺(+)-valiolamine及其差向异构体(-)-1-epi-valiolamine:
从莽草酸出发,经过成酯反应,以97%的收率得到莽草酸乙酯I-B-2,它与SOCl2在DMF溶液中反应,由于莽草酸乙酯I-B-2的3位羟基活性较高,能被氯取代,而4、5位的羟基则被甲酰化,以91%的收率,立体专一性地得到3位氯代产物I-B-3；莽草酸乙酯I-B-2与苯甲醛反应形成缩醛I-B-21后经NBS开环(两步一锅法),以90%的收率得到溴代产物I-B-22。I-B-3与I-B-22都可以在碱的作用下,脱去保护基,分子内取代,得到3、4位环氧化合物I-B-4。化合物I-B-4经过甲磺酰化后得到I-B-5,它在三氟醋酸与水混合溶液中,会发生环氧开环反应,以93%的收率单一地得到二醇化合物I-B-6。此化合物在醋酸存在下与叠氮钠在DMSO中反应,会经过一个SN2反应机理,以83%的收率得到叠氮取代化合物I-B-7a,其5位的构型发生转化；而在乙醇溶液中,会先发生分子内取代反应得到环氧化合物,接着环氧被叠氮基开环,以84%的收率得到化合物1-B-7b,其5位的构型保持不变。接着在I-B-7a和I-B-7b的烯丙位羟基用T3DPS基团保护,并还原酯基,再用乙酰基保护其它羟基后得到化合物I-B-9a和I-B-9b。I-B-9a和I-B-9b的双键经RuCl3/NaIO4作用双羟化后得到多羟基化合物1-B-10a和I-B-10b,最后脱去保护基并用Pd/C还原叠氮基成胺基,就合成了井冈霉醇胺(+)-valiolamine I-A-1及其差向异构体(-)-1-epi-valiolamine I-A-4。从莽草酸出发,分别经过十二步,最终以35%的总收率得到了化合物I-A-1,并以30%的总收率得到化合物1-A-4。
(2)第二部分描述了从莽草酸出发合成四个重要手性环氧中间体(H-A-1、Ⅱ-A-2、Ⅱ-A-3、 Ⅱ-A-4):
(a)莽草酸成甲酯后,利用二氯亚砜保护莽草酸甲酯3、4位羟基,得到环状亚硫酸酯II-B-1,把其5位羟基甲磺酰化后,以96%的收率得到化合物11-B-2,在碳酸钾的作用下,脱去其亚硫酸酯,分子内取代,以90%的收率合成了环氧化合物II-A-1；
(b)用酸脱去化合物II-B-2上的亚硫酸酯后,以95%的收率得到二羟基化合物II-B-7,利用其烯丙位位阻小的特性,选择性地把3位羟磺酰化,以86%的收率得到化合物II-B-8,它在BzOH/Et3N (3:2)作用下,3位以上的OTs基团被OBz基团取代,构型发生翻转,以85%的收率得到化合物II-B-9,最后在碱的作用下脱去苯甲酰基,分子内取代,以93%的收率得到环氧化合物II-A-2。
(c)化合物II-B-1的5位羟基苯甲酰化得到化合物11-B-1１,用酸脱去亚硫酸酯后得到二羟基化合物II-B-12,经双甲磺酰化反应,得到化合物II-B-13,利用其烯丙位的高活性,在AcOH和DBU的混合物(3：1)的作用下,化合物II-B-133位的OMs基团被OAc基团取代,以86%的收率得到化合物11-B-14,它在碱的作用下脱去乙酰基和苯甲酰基,分子内取代,以90%的收率得到环氧化合物II-A-3。
(d)化合物II-B-12的3位位阻小,选择性地用对氯苯甲酰氯对II-B-12的3位羟基进行酰化,以88%的收率得到化合物II-B-18,其4位上的羟基经甲烷磺酰化得到化合物II-B-19,在碱的作用下,脱去保护基,分子内成环,以90%的收率合成了环氧化合物II-A-4。
总之,以莽草酸为原料,经过四步反应,以79%的总收率得到环氧化合物11-A-1,经过七步反应,分别以56%、64%、65%的总收率得到脱水莽草酸甲酯类手性环氧化合物Ⅱ-A-2、Ⅱ-A-3、Ⅱ-A-4。
(3)第三部分描述了氯化铜使肟、腙转化为羰基化合物的绿色化学方法：
研究了不同取代的肟、腙在各种铜盐催化下,于不同溶剂中进行水解,生成相应的羰基化合物的方法。其中最佳条件是在二当量氯化铜的作用下,于乙腈和水(4：1)的混合溶剂中回流。不取代的肟、腙经水解以85-98%的收率得到相应的羰基化合物。此方法对各种敏感基团(含硫基团、醛基等)没有影响,反应条件温和、收率高,后处理简单。且反应中的氯化铜经回收后能继续循环利用,符合绿色化学概念。
This dissertation contains the following three parts:
(1) In the first part,(+)-valiolamine and its epimer (-)-1-epi-valiolamine were synthesized from the naturally abundant (-)-shikimic acid:
Starting from (-)-shikimic acid, ethyl shikimate I-B-2was first prepared in97%yield, and then was treated with thionyl chloride in N,N-dimethylformamide (DMF). Because of the better reaction of the hydroxyl group at the allylic (C-3) position than the other two hydroxyls at C-4and C-5, a highly regioselective chlorination of the C-3hydroxyl took place. Then, both hydroxyls at C-4and C-5were masked by formyl groups. As a result, compound I-B-3was obtained in91%yield. Ethyl shikimate I-B-2was first treated with PhCHO to give an acetal I-B-21, which was then treated with NBS to afford bromide I-B-22in90%yield. When both compounds I-B-3and I-B-22were treated with K2CO3,3,4-epoxido compound I-B-4could be smoothly obtained after deblocking and intermolecular substitution. Methanesulfonylation of epoxide I-B-4gave I-B-5, which then underwent ring-opening in aqueous CF3COOH to give compound I-B-6in93%yield. Compound I-B-6was treated with sodium azide in the presence of0.5equivalent of AcOH by using dimethylsulfoxide (DMSO) as the solvent. A typical SN2-type nucleophilic substitution occurred smoothly to afford compound I-B-7a in83%yield, and the (R) configuration of C-5was inverted to (S) via a Walden-type inversion. In contrast, when compound I-B-6was treated with sodium azide at reflux by using ethanol as the solvent, compound I-B-7b was obtained in84%yield, but the (R) configuration of C-5retained during the substitution. Subsequently, protection of hydroxyl groups at the allyllie (C-3) position of compounds I-B-7a and I-B-7b by TBDPS, reduction of ester groups, and acylation of the other hydroxyl groups smoothly afforded compounds I-B-9a and I-B-9b. Then, Ru-catalyzed asymmetric dihydroxylation of compounds I-B-9a and I-B-9b was proceeded smoothly to afford compounds I-B-10a and I-B-10b. Finally, after removal of all the protecting groups followed by Pd/C-catalyzed hydrogenation of the azido group,(+)-valiolamine I-A-1and (-)-1-epi-valiolamine I-A-4were obtained accordingly.
In conclusion, by using the naturally abundant (-)-shikimic acid as the starting matrial, the first target compound (+)-valiolamine I-A-1was synthesized via12steps in35%overall yield, and the second target compound (-)-1-epi-valiolamine I-A-4via12steps in30% overall yield.
(2) In the second part, syntheses of four important chiral epoxy intermediates from the naturally abundant (-)-shikimic acid were described:
(a) Starting from (-)-shikimic acid, we first prepared cyclic sulfite intermediate Ⅱ-B-1by protecting3,4-dihydroxyl groups with SOCl2Methanesulfonylation of hydroxyl at C-5of compound Ⅱ-B-1gave compound Ⅰ-B-2in96%yield. Compound Ⅱ-B-2was treated with powdered potassium carbonate in anhydrous methanol, and cascade methanolysis of cyclic sulfite and intramolecular SN2-type reaction took place smoothly to afford the desired epoxide Ⅱ-A-1.
(b) Compound Ⅱ-B-2was treated with aqueous concentrated hydrochloric acid, the cyclic sulfite functional group of compounds Ⅱ-B-2was thus removed, and compound Ⅱ-B-7was obtained in95%yield. Regioselective mono-tosylation of the less-hindered hydroxyl group at C-3of compound Ⅱ-B-7with toluenesulfonyl chloride produced tosylate Ⅱ-B-8. After the treatment of compound Ⅱ-B-8with a mixture of benzoic acid and triethylamine (BzOH/Et3N=3:2), nucleophilic substitution of OTs group at C-3allylic position of compound Ⅱ-B-8afforded benzoate Ⅱ-B-9in85%yield. When compound Ⅱ-B-9was treated with potassium carbonate, epoxide formation and a simultaneous deblocking of benzoyl group took place smoothly to give the desired epoxide Ⅱ-A-2in93%yield.
(c) Protection of hydroxyl group at C-5of compound Ⅱ-B-1with BzCI afforded compound Ⅱ-B-11. Then treatment with aqueous concentrated hydrochloric acid to remove the cyclic sulfite functional group of compounds Ⅱ-B-11provided compound II-B-12. Compound Ⅱ-B-12reacted with methanesulfonyl chloride to produce the bismesylated compound Ⅱ-B-13. Compound Ⅱ-B-13was treated with a mixture of AcOH and DBU (AcOH/DBU=3:1), where a selective SN2-type replacement of the OMs group at C-3position by an OAc group took place smoothly to afford compound Ⅱ-B-14in86%yield. Treatment of compound Ⅱ-B-14with K2CO3furnished the desired epoxide Ⅱ-A-3.
(d) Compound Ⅱ-B-12was exposed to p-hlorobenzoyl chloride, and selective protection of the less hindered hydroxyl at allylic C-3position took place smoothly to afford compound Ⅱ-B-18in88%yield. Methanesulfonylation of hydroxyl group at C-4of compound Ⅱ-B-18with methanesulfonyl chloride produced compound Ⅱ-B-19. Then removal of the protecting groups followed by an intramolecular substitution finally furnished epoxide Ⅱ-A-4in90%yield.
In summary, we have successfully developed novel asymmetric syntheses of four useful chiral epoxides Ⅱ-A-1, Ⅱ-A-2, Ⅱ-A-3, Ⅱ-A-4from (-)-shikimic acid in79%(over4steps). 56%(7steps),64%(7steps) and65%(7steps) overall yields, respectively.
(3) In the third part, we described a green method for the regeneration of carbonyl compounds from oximes and hydrazones by using cupric chloride dihydrate as a recoverable promoter for hydrolysis:
We investigated the hydrolysis of oximes and hydrazones with various cupric salts in different solvents to obtain the corresponding carbonyl compounds. The best condition was found as follows:2molar equivalent of cupric chloride dihydrate (CuCl2·2H2O) used in an aqueous acetonitrile (CH3CN/H2O=4:1) at reflux. The comesponding carboxyl compounds were obtained in85-98%yields. This method is tolerant with various sensitive groups (sulfides, aldehydes, etc). In addition, cupric salt could readily be recovered in almost quantitative yield via the complete precipitation of Cu(OH)2, which could be reused for the above hydrolysis after being converted int.
(1)第一部分描述了从莽草酸出发合成糖苷酶抑制剂井冈霉醇胺(+)-valiolamine及其差向异构体(-)-1-epi-valiolamine:
从莽草酸出发,经过成酯反应,以97%的收率得到莽草酸乙酯I-B-2,它与SOCl2在DMF溶液中反应,由于莽草酸乙酯I-B-2的3位羟基活性较高,能被氯取代,而4、5位的羟基则被甲酰化,以91%的收率,立体专一性地得到3位氯代产物I-B-3；莽草酸乙酯I-B-2与苯甲醛反应形成缩醛I-B-21后经NBS开环(两步一锅法),以90%的收率得到溴代产物I-B-22。I-B-3与I-B-22都可以在碱的作用下,脱去保护基,分子内取代,得到3、4位环氧化合物I-B-4。化合物I-B-4经过甲磺酰化后得到I-B-5,它在三氟醋酸与水混合溶液中,会发生环氧开环反应,以93%的收率单一地得到二醇化合物I-B-6。此化合物在醋酸存在下与叠氮钠在DMSO中反应,会经过一个SN2反应机理,以83%的收率得到叠氮取代化合物I-B-7a,其5位的构型发生转化；而在乙醇溶液中,会先发生分子内取代反应得到环氧化合物,接着环氧被叠氮基开环,以84%的收率得到化合物1-B-7b,其5位的构型保持不变。接着在I-B-7a和I-B-7b的烯丙位羟基用T3DPS基团保护,并还原酯基,再用乙酰基保护其它羟基后得到化合物I-B-9a和I-B-9b。I-B-9a和I-B-9b的双键经RuCl3/NaIO4作用双羟化后得到多羟基化合物1-B-10a和I-B-10b,最后脱去保护基并用Pd/C还原叠氮基成胺基,就合成了井冈霉醇胺(+)-valiolamine I-A-1及其差向异构体(-)-1-epi-valiolamine I-A-4。从莽草酸出发,分别经过十二步,最终以35%的总收率得到了化合物I-A-1,并以30%的总收率得到化合物1-A-4。
(2)第二部分描述了从莽草酸出发合成四个重要手性环氧中间体(H-A-1、Ⅱ-A-2、Ⅱ-A-3、 Ⅱ-A-4):
(a)莽草酸成甲酯后,利用二氯亚砜保护莽草酸甲酯3、4位羟基,得到环状亚硫酸酯II-B-1,把其5位羟基甲磺酰化后,以96%的收率得到化合物11-B-2,在碳酸钾的作用下,脱去其亚硫酸酯,分子内取代,以90%的收率合成了环氧化合物II-A-1；
(b)用酸脱去化合物II-B-2上的亚硫酸酯后,以95%的收率得到二羟基化合物II-B-7,利用其烯丙位位阻小的特性,选择性地把3位羟磺酰化,以86%的收率得到化合物II-B-8,它在BzOH/Et3N (3:2)作用下,3位以上的OTs基团被OBz基团取代,构型发生翻转,以85%的收率得到化合物II-B-9,最后在碱的作用下脱去苯甲酰基,分子内取代,以93%的收率得到环氧化合物II-A-2。
(c)化合物II-B-1的5位羟基苯甲酰化得到化合物11-B-1１,用酸脱去亚硫酸酯后得到二羟基化合物II-B-12,经双甲磺酰化反应,得到化合物II-B-13,利用其烯丙位的高活性,在AcOH和DBU的混合物(3：1)的作用下,化合物II-B-133位的OMs基团被OAc基团取代,以86%的收率得到化合物11-B-14,它在碱的作用下脱去乙酰基和苯甲酰基,分子内取代,以90%的收率得到环氧化合物II-A-3。
(d)化合物II-B-12的3位位阻小,选择性地用对氯苯甲酰氯对II-B-12的3位羟基进行酰化,以88%的收率得到化合物II-B-18,其4位上的羟基经甲烷磺酰化得到化合物II-B-19,在碱的作用下,脱去保护基,分子内成环,以90%的收率合成了环氧化合物II-A-4。
总之,以莽草酸为原料,经过四步反应,以79%的总收率得到环氧化合物11-A-1,经过七步反应,分别以56%、64%、65%的总收率得到脱水莽草酸甲酯类手性环氧化合物Ⅱ-A-2、Ⅱ-A-3、Ⅱ-A-4。
(3)第三部分描述了氯化铜使肟、腙转化为羰基化合物的绿色化学方法：
研究了不同取代的肟、腙在各种铜盐催化下,于不同溶剂中进行水解,生成相应的羰基化合物的方法。其中最佳条件是在二当量氯化铜的作用下,于乙腈和水(4：1)的混合溶剂中回流。不取代的肟、腙经水解以85-98%的收率得到相应的羰基化合物。此方法对各种敏感基团(含硫基团、醛基等)没有影响,反应条件温和、收率高,后处理简单。且反应中的氯化铜经回收后能继续循环利用,符合绿色化学概念。
This dissertation contains the following three parts:
(1) In the first part,(+)-valiolamine and its epimer (-)-1-epi-valiolamine were synthesized from the naturally abundant (-)-shikimic acid:
Starting from (-)-shikimic acid, ethyl shikimate I-B-2was first prepared in97%yield, and then was treated with thionyl chloride in N,N-dimethylformamide (DMF). Because of the better reaction of the hydroxyl group at the allylic (C-3) position than the other two hydroxyls at C-4and C-5, a highly regioselective chlorination of the C-3hydroxyl took place. Then, both hydroxyls at C-4and C-5were masked by formyl groups. As a result, compound I-B-3was obtained in91%yield. Ethyl shikimate I-B-2was first treated with PhCHO to give an acetal I-B-21, which was then treated with NBS to afford bromide I-B-22in90%yield. When both compounds I-B-3and I-B-22were treated with K2CO3,3,4-epoxido compound I-B-4could be smoothly obtained after deblocking and intermolecular substitution. Methanesulfonylation of epoxide I-B-4gave I-B-5, which then underwent ring-opening in aqueous CF3COOH to give compound I-B-6in93%yield. Compound I-B-6was treated with sodium azide in the presence of0.5equivalent of AcOH by using dimethylsulfoxide (DMSO) as the solvent. A typical SN2-type nucleophilic substitution occurred smoothly to afford compound I-B-7a in83%yield, and the (R) configuration of C-5was inverted to (S) via a Walden-type inversion. In contrast, when compound I-B-6was treated with sodium azide at reflux by using ethanol as the solvent, compound I-B-7b was obtained in84%yield, but the (R) configuration of C-5retained during the substitution. Subsequently, protection of hydroxyl groups at the allyllie (C-3) position of compounds I-B-7a and I-B-7b by TBDPS, reduction of ester groups, and acylation of the other hydroxyl groups smoothly afforded compounds I-B-9a and I-B-9b. Then, Ru-catalyzed asymmetric dihydroxylation of compounds I-B-9a and I-B-9b was proceeded smoothly to afford compounds I-B-10a and I-B-10b. Finally, after removal of all the protecting groups followed by Pd/C-catalyzed hydrogenation of the azido group,(+)-valiolamine I-A-1and (-)-1-epi-valiolamine I-A-4were obtained accordingly.
In conclusion, by using the naturally abundant (-)-shikimic acid as the starting matrial, the first target compound (+)-valiolamine I-A-1was synthesized via12steps in35%overall yield, and the second target compound (-)-1-epi-valiolamine I-A-4via12steps in30% overall yield.
(2) In the second part, syntheses of four important chiral epoxy intermediates from the naturally abundant (-)-shikimic acid were described:
(a) Starting from (-)-shikimic acid, we first prepared cyclic sulfite intermediate Ⅱ-B-1by protecting3,4-dihydroxyl groups with SOCl2Methanesulfonylation of hydroxyl at C-5of compound Ⅱ-B-1gave compound Ⅰ-B-2in96%yield. Compound Ⅱ-B-2was treated with powdered potassium carbonate in anhydrous methanol, and cascade methanolysis of cyclic sulfite and intramolecular SN2-type reaction took place smoothly to afford the desired epoxide Ⅱ-A-1.
(b) Compound Ⅱ-B-2was treated with aqueous concentrated hydrochloric acid, the cyclic sulfite functional group of compounds Ⅱ-B-2was thus removed, and compound Ⅱ-B-7was obtained in95%yield. Regioselective mono-tosylation of the less-hindered hydroxyl group at C-3of compound Ⅱ-B-7with toluenesulfonyl chloride produced tosylate Ⅱ-B-8. After the treatment of compound Ⅱ-B-8with a mixture of benzoic acid and triethylamine (BzOH/Et3N=3:2), nucleophilic substitution of OTs group at C-3allylic position of compound Ⅱ-B-8afforded benzoate Ⅱ-B-9in85%yield. When compound Ⅱ-B-9was treated with potassium carbonate, epoxide formation and a simultaneous deblocking of benzoyl group took place smoothly to give the desired epoxide Ⅱ-A-2in93%yield.
(c) Protection of hydroxyl group at C-5of compound Ⅱ-B-1with BzCI afforded compound Ⅱ-B-11. Then treatment with aqueous concentrated hydrochloric acid to remove the cyclic sulfite functional group of compounds Ⅱ-B-11provided compound II-B-12. Compound Ⅱ-B-12reacted with methanesulfonyl chloride to produce the bismesylated compound Ⅱ-B-13. Compound Ⅱ-B-13was treated with a mixture of AcOH and DBU (AcOH/DBU=3:1), where a selective SN2-type replacement of the OMs group at C-3position by an OAc group took place smoothly to afford compound Ⅱ-B-14in86%yield. Treatment of compound Ⅱ-B-14with K2CO3furnished the desired epoxide Ⅱ-A-3.
(d) Compound Ⅱ-B-12was exposed to p-hlorobenzoyl chloride, and selective protection of the less hindered hydroxyl at allylic C-3position took place smoothly to afford compound Ⅱ-B-18in88%yield. Methanesulfonylation of hydroxyl group at C-4of compound Ⅱ-B-18with methanesulfonyl chloride produced compound Ⅱ-B-19. Then removal of the protecting groups followed by an intramolecular substitution finally furnished epoxide Ⅱ-A-4in90%yield.
In summary, we have successfully developed novel asymmetric syntheses of four useful chiral epoxides Ⅱ-A-1, Ⅱ-A-2, Ⅱ-A-3, Ⅱ-A-4from (-)-shikimic acid in79%(over4steps). 56%(7steps),64%(7steps) and65%(7steps) overall yields, respectively.
(3) In the third part, we described a green method for the regeneration of carbonyl compounds from oximes and hydrazones by using cupric chloride dihydrate as a recoverable promoter for hydrolysis:
We investigated the hydrolysis of oximes and hydrazones with various cupric salts in different solvents to obtain the corresponding carbonyl compounds. The best condition was found as follows:2molar equivalent of cupric chloride dihydrate (CuCl2·2H2O) used in an aqueous acetonitrile (CH3CN/H2O=4:1) at reflux. The comesponding carboxyl compounds were obtained in85-98%yields. This method is tolerant with various sensitive groups (sulfides, aldehydes, etc). In addition, cupric salt could readily be recovered in almost quantitative yield via the complete precipitation of Cu(OH)2, which could be reused for the above hydrolysis after being converted int.
引文
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