烷氧基联苯类化合物的合成及抗病毒活性研究
摘要
以4，4′-二甲氧基-5，6，5′，6′-二亚甲二氧基联苯为先导化合物，构建了两类由取代苄基哌嗪修饰的新型烷氧基联苯化合物，测定了部分化合物的抗病毒活性；为构建联苯分子骨架，对烷氧基溴苯的偶合方法进行了研究；通过直接不对称Ullmann偶合或Ullmann-type偶合反应及构象转化方法制备了轴手性烷氧基联苯化合物。
1．第一类化合物建立在先导化合物4，4′-二甲氧基-5，6，5′，6′-二亚甲二氧基联苯′2，2′-二甲酸二甲酯的基础上。首先，由2-溴-3，4-亚甲二氧基-5-甲氧基-苯甲酸甲酯在活性铜或镍的作用下偶合得到4，4′二甲氧基-5，6，5′，6′-二亚甲二氧基联苯-2，2′-二甲酸二甲酯，再转化为三种4，4′-二甲氧基-5，6，5′，6′-二亚甲二氧基联苯-2，2′-二甲酸单酯。然后与另外制备的取代苄基哌嗪进行反应，在DMAP，DCC的作用下生成新化合物4，4′-二甲氧基-5，6，5′，6′-二亚甲二氧基-2-烷氧甲酰基-2′-(4-取代苯甲基-哌嗪-1-羰基)-联苯。采取NMR，ESI-MS，IR等手段进行了结构确证。
选取部分化合物进行抗SIV活性测定，结果表明，合成的新化合物具有不同程度的抑制SIV活性，并且细胞毒性较小。浓度7.8μg／mL时，化合物2-24，2-30，2-42，分别表现出47.4，38.0，32.3％的病毒抗原细胞抑制率，尤其是化合物2-20表现出较高的活性，浓度2.0μg／mL(2.9μM)时，病毒抗原细胞抑制率达44.7％。
2．为制备第二类烷氧基联苯化合物，关键中间体4，4′-二甲氧基-5，6，5′，6′-二亚甲二氧基-2-羟甲基-2′-烷氧甲酰基联苯由两种途径制得。硼氢化钠-碘直接
选择性还原4，4，一二甲氧基一5，6，5‘，6，一二亚甲二氧基联苯一2，2‘一二甲酸单酷的游
离梭基;或在曝吩一2一甲酸亚铜的作用下，2一嗅一5一甲氧基一3，4一亚甲二氧基苯甲酸
一2‘一澳一5‘一甲氧基一3’，4‘一亚甲二氧基节酷进行分子内偶合及醇解。4，4’一二甲氧基
一5，6，5’，6’一二亚甲二氧基一2一轻甲基一2’一烷氧甲酞基联苯经氯乙酸酷化后，与取
代节基呱嗦作用生成第二类化合物。利用ID，ZD NMR，ES工一MS对化合物的结构
进行了确证。
o//‘\o
COOMeO
COOMeO
O勺份0
o/产、J、、o
Rl=H;4一F;4一CI;4一Br;4一MeO;3，4一di MeO
3.利用铜作用下的Ullinann偶合及镍作用下的类Ullmann偶合方法制备了
手性4，4‘一二甲氧基一5，6，5，，6‘一二亚甲二氧基一2，2，一二唔哇琳联苯。2一澳一3，4-
亚甲二氧基一5一甲氧基一苯甲酸甲醋经水解、酞氯化、与L一2一氨基丙醇进行酞胺
化反应、醇经基氯代、碱性条件下成环得手性中间体(S卜2一(2一溟一5一甲氧基一3，4一亚
甲二氧基苯基关4一甲基嗯哇琳一(简称(S关嗯哇琳澳苯)，(S)一嗯哇琳溟苯在活性铜作
用下进行立体选择性Ullm撇偶合反应，生成了以S构型为主的4，4，一二甲氧基
一5，6，5‘，6’一二亚甲二氧基一2，2’一二嗓哇琳联苯。
4.首次将Ni(即h3)2CI/Zn/NaH偶合剂用于两个邻位取代基分别为亚甲氧基
和手性嗒哩琳基团的澳代苯的偶合。(S)一2一(4一甲基嗯哇琳基关4一甲氧基一5，6一亚甲二
氧基嗅苯在偶合剂Ni(PPh3)3C12/Z川NaH作用下，于甲苯中进行不对称偶合，生
成轴手性S或R构型过量的非对映异构体二嗦哇琳联苯。随Ni(P Ph小Cl:加入量
的不同，二嚷哇琳联苯的总转化率、主要产物的构型均发生变化。以嗯哇琳-
e
M
O
O
C
e七夕
M资声
O||人、f
澳苯的用量计算，使用等摩尔的Ni(P Ph扔C12，则偶合产物以联苯S构型为优势;
使用0.5 equlv.的Ni(PPh3)3C12，则偶合产物以联苯R构型为优势，但偶合转化率
较低。
5.由光学纯(S)一4，4‘一二甲氧基一5，6，5‘，6‘一二亚甲二氧基一2，2，一二((S)一4-
甲基嚷哇琳)制备了轴手性(S)一4，4‘一二甲氧基一5，6，5‘，6‘一二亚甲二氧基联苯
一2，2‘一二甲酸二甲酉旨。
6.本文还考察了手性嗯哇琳基团对消旋4，4’一二甲氧基一5，6，5‘，6‘一二亚甲二
氧基联苯手性轴的影响。消旋4，4‘一二甲氧基一5，6，5，，6‘一二亚甲二氧基联苯一
2，2‘一二甲酸甲酷，经水解、酞氯化、与(S)一2一氨基丙醇反应成酞胺、轻基氯代、
环化得4，4‘一二甲氧基一5，6，5‘，6‘一二亚甲二氧基一2，2‘一二((S)一4一甲基嚷哇琳)联
苯。HPLC分析表明，其两个非对映异构体的比率为1:1。甲苯中，在碘化亚铜作
用下，非对映异构体混合物转化为轴手性为S构型的单一异构体。
e
M
O
O
U
e卜夕
M谈厂
01人z\丫
亘
︶八
/吸\
<。沈夕
n~产r产~、女卜向
COOMe
oMe oMe 6Me
7.对铜作用下及镍作用下的立体选择性Ullmann偶合及Unm~一tyPe偶合
的机理、对一Cul作用下(R/S)4，4‘一二甲氧基一5，6，5‘，6’一二亚甲二氧基一2，2‘一二
((S)一4一甲基德哇琳)联苯构象转化机理进行了探讨。
本沦文工作共计合成化合物91个，其中新?
Based on the similar structure of alkyloxy-biphenyl compounds with biological activity, two kinds of new biphenyl compounds containing alkyloxy-biphenyl modified by substituted benzylpiperazine were designed and synthesized by parallel synthesis. Anti-virus activity of some biphenyls was examined. The Ullmann-type coupling reaction to synthesize alkyloxy-biphenyl was carried out in the presence of Ni(PPh3)2Cl/Zn/NaH. Moreover, Chiral 4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-biphenyl were afforded through asymmetric coupling reaction of arylbromide or configuration transform of corresponding compound.
The first kind of compounds were synthesized, Based on the lead compound, dimethyl-4,4'-dimethoxy-5,6,5', 6'-dimethenedioxy-biphenyl-2, 2'-dicarbonylate. At first, dimethyl-4, 4'-dimethoxy-5, 6, 5', 6'-dimethenedioxy-biphenyl-2,2'- dicarbony-late were synthesized through coupling reaction of methyl 2-bromo-3,4-methenedi-oxy-5-methoxy-benzene carbonylate in the presence of active copper or coupling agent Ni(PPh3)2Cl/Zn/NaH in good yield, and then it was converted to 4,4' -dimethoxy-5,6,5' ,6' -dimethenedioxy-biphenyl-2-alkyloxycarbonyl-2' -carboxylic acid. The compounds have been further modified by substituted N-benzyl piperazines to afford corresponding novel biphenyls. The structure of these new compounds was confirmed by 1H NMR, IR and ESI-MS.
Activity, against simian immunodeficiency virus, of some novel biphenyl compounds, was tested in vitro. All of those showed activity of anti-virus. At the compounds concentration of 7.8 ug/mL, compounds, 2-24, 2-30, 2-42, showed 47.4,
38.0, 32.3% reduction in antigen, respectively. Among the three compounds, compound 2-24 possesses the more potent anti-HIV activity. It is noticeable that compound 2-20 exhibit 44.7% reduction in antigen at concentration of 2.0 u.g/mL(2.9uM).
The second type of novel compounds, 4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-2-(2-(4-substituted-benzyl~piperazine-l-yl-)-acetoxymethyl)-2'-methoxycarbonyl-biphenyl, were synthesized. The key intermediate, 4,4'-dimethoxy-5,6,5',6'-dimethenedioxyl-2-hydroxymethyl-2'-methoxycarbonyl-biphenyl, was prepared by two methods. One method was selective reduction of methyl-4,4'-dimethoxy-5,6,5', 6'-dimethenedioxy-biphenyl-2,2'-dicarbonylate by NaBH4-I2. The second was intramolecular coupling of 2-bromo-5-methoxy-3,4- methenedioxybenzyl 2-bromo-5-methoxy-3,4-methenedioxybenzoate in the presence of activated copper or CuTC. The structure of the aimed compounds was confirmed by means of 1H NMR, 13C NMR, HSQC, HMBC, NOESY and ESI-MS.
(S)-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-2,2'-di-(4(S)-methyl-oxazoline-l)-biphenyl was synthesized through asymmetric Ullmann coupling reaction or asymmetric Ullmann-type coupling reaction in the presence of Ni(PPh3)2Cl/Zn/NaH.
In the thesis, it was found for the first time that the arylbromide with ortho metheneoxy and chiral oxazoline group can couple to give corresponding biphenyl in the presence of Ni(PPh3)2Cl/Zn/NaH. In the asymmetric Ullmann-type, It was noticeable that which was excessive among the biphenyl with S or R configuration was dependent on ratio of Ni(PPh3)2Cl2 to aryl bromide. 0.5 equiv Ni(PPh3)2Cl2 gave
excessive R and 1 equiv or more Ni(PPh3)2Cl2 afforded excessive S. The different stereoselectivity should reflect two kinds of coupling mechanism, intermolecular and intramolecular coupling of Ni-complex intermediate.
we have also found another efficacious method to prepare (S)-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-2,2'-di-[4(S)-methyl-oxazoline-l]-biph enyl through configuration transform of (R/S)-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-2,2'-di-(4(S)-methyl-oxazoline-l)-bi-biphenyl in excellent yield promoted by interaction between chiral oxazolines moiety of biphenyl and Cu(I). (S)-dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-biphen-yl-2,2'-dicarboxylate was prepared from (S)-2,2'-dioxazoline biphenyl isomer conveniently.
At last, the mechanism of asymmetric Ullmann coupling, asymmetric Ullmann-t
1．第一类化合物建立在先导化合物4，4′-二甲氧基-5，6，5′，6′-二亚甲二氧基联苯′2，2′-二甲酸二甲酯的基础上。首先，由2-溴-3，4-亚甲二氧基-5-甲氧基-苯甲酸甲酯在活性铜或镍的作用下偶合得到4，4′二甲氧基-5，6，5′，6′-二亚甲二氧基联苯-2，2′-二甲酸二甲酯，再转化为三种4，4′-二甲氧基-5，6，5′，6′-二亚甲二氧基联苯-2，2′-二甲酸单酯。然后与另外制备的取代苄基哌嗪进行反应，在DMAP，DCC的作用下生成新化合物4，4′-二甲氧基-5，6，5′，6′-二亚甲二氧基-2-烷氧甲酰基-2′-(4-取代苯甲基-哌嗪-1-羰基)-联苯。采取NMR，ESI-MS，IR等手段进行了结构确证。
选取部分化合物进行抗SIV活性测定，结果表明，合成的新化合物具有不同程度的抑制SIV活性，并且细胞毒性较小。浓度7.8μg／mL时，化合物2-24，2-30，2-42，分别表现出47.4，38.0，32.3％的病毒抗原细胞抑制率，尤其是化合物2-20表现出较高的活性，浓度2.0μg／mL(2.9μM)时，病毒抗原细胞抑制率达44.7％。
2．为制备第二类烷氧基联苯化合物，关键中间体4，4′-二甲氧基-5，6，5′，6′-二亚甲二氧基-2-羟甲基-2′-烷氧甲酰基联苯由两种途径制得。硼氢化钠-碘直接
选择性还原4，4，一二甲氧基一5，6，5‘，6，一二亚甲二氧基联苯一2，2‘一二甲酸单酷的游
离梭基;或在曝吩一2一甲酸亚铜的作用下，2一嗅一5一甲氧基一3，4一亚甲二氧基苯甲酸
一2‘一澳一5‘一甲氧基一3’，4‘一亚甲二氧基节酷进行分子内偶合及醇解。4，4’一二甲氧基
一5，6，5’，6’一二亚甲二氧基一2一轻甲基一2’一烷氧甲酞基联苯经氯乙酸酷化后，与取
代节基呱嗦作用生成第二类化合物。利用ID，ZD NMR，ES工一MS对化合物的结构
进行了确证。
o//‘\o
COOMeO
COOMeO
O勺份0
o/产、J、、o
Rl=H;4一F;4一CI;4一Br;4一MeO;3，4一di MeO
3.利用铜作用下的Ullinann偶合及镍作用下的类Ullmann偶合方法制备了
手性4，4‘一二甲氧基一5，6，5，，6‘一二亚甲二氧基一2，2，一二唔哇琳联苯。2一澳一3，4-
亚甲二氧基一5一甲氧基一苯甲酸甲醋经水解、酞氯化、与L一2一氨基丙醇进行酞胺
化反应、醇经基氯代、碱性条件下成环得手性中间体(S卜2一(2一溟一5一甲氧基一3，4一亚
甲二氧基苯基关4一甲基嗯哇琳一(简称(S关嗯哇琳澳苯)，(S)一嗯哇琳溟苯在活性铜作
用下进行立体选择性Ullm撇偶合反应，生成了以S构型为主的4，4，一二甲氧基
一5，6，5‘，6’一二亚甲二氧基一2，2’一二嗓哇琳联苯。
4.首次将Ni(即h3)2CI/Zn/NaH偶合剂用于两个邻位取代基分别为亚甲氧基
和手性嗒哩琳基团的澳代苯的偶合。(S)一2一(4一甲基嗯哇琳基关4一甲氧基一5，6一亚甲二
氧基嗅苯在偶合剂Ni(PPh3)3C12/Z川NaH作用下，于甲苯中进行不对称偶合，生
成轴手性S或R构型过量的非对映异构体二嗦哇琳联苯。随Ni(P Ph小Cl:加入量
的不同，二嚷哇琳联苯的总转化率、主要产物的构型均发生变化。以嗯哇琳-
e
M
O
O
C
e七夕
M资声
O||人、f
澳苯的用量计算，使用等摩尔的Ni(P Ph扔C12，则偶合产物以联苯S构型为优势;
使用0.5 equlv.的Ni(PPh3)3C12，则偶合产物以联苯R构型为优势，但偶合转化率
较低。
5.由光学纯(S)一4，4‘一二甲氧基一5，6，5‘，6‘一二亚甲二氧基一2，2，一二((S)一4-
甲基嚷哇琳)制备了轴手性(S)一4，4‘一二甲氧基一5，6，5‘，6‘一二亚甲二氧基联苯
一2，2‘一二甲酸二甲酉旨。
6.本文还考察了手性嗯哇琳基团对消旋4，4’一二甲氧基一5，6，5‘，6‘一二亚甲二
氧基联苯手性轴的影响。消旋4，4‘一二甲氧基一5，6，5，，6‘一二亚甲二氧基联苯一
2，2‘一二甲酸甲酷，经水解、酞氯化、与(S)一2一氨基丙醇反应成酞胺、轻基氯代、
环化得4，4‘一二甲氧基一5，6，5‘，6‘一二亚甲二氧基一2，2‘一二((S)一4一甲基嚷哇琳)联
苯。HPLC分析表明，其两个非对映异构体的比率为1:1。甲苯中，在碘化亚铜作
用下，非对映异构体混合物转化为轴手性为S构型的单一异构体。
e
M
O
O
U
e卜夕
M谈厂
01人z\丫
亘
︶八
/吸\
<。沈夕
n~产r产~、女卜向
COOMe
oMe oMe 6Me
7.对铜作用下及镍作用下的立体选择性Ullmann偶合及Unm~一tyPe偶合
的机理、对一Cul作用下(R/S)4，4‘一二甲氧基一5，6，5‘，6’一二亚甲二氧基一2，2‘一二
((S)一4一甲基德哇琳)联苯构象转化机理进行了探讨。
本沦文工作共计合成化合物91个，其中新?
Based on the similar structure of alkyloxy-biphenyl compounds with biological activity, two kinds of new biphenyl compounds containing alkyloxy-biphenyl modified by substituted benzylpiperazine were designed and synthesized by parallel synthesis. Anti-virus activity of some biphenyls was examined. The Ullmann-type coupling reaction to synthesize alkyloxy-biphenyl was carried out in the presence of Ni(PPh3)2Cl/Zn/NaH. Moreover, Chiral 4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-biphenyl were afforded through asymmetric coupling reaction of arylbromide or configuration transform of corresponding compound.
The first kind of compounds were synthesized, Based on the lead compound, dimethyl-4,4'-dimethoxy-5,6,5', 6'-dimethenedioxy-biphenyl-2, 2'-dicarbonylate. At first, dimethyl-4, 4'-dimethoxy-5, 6, 5', 6'-dimethenedioxy-biphenyl-2,2'- dicarbony-late were synthesized through coupling reaction of methyl 2-bromo-3,4-methenedi-oxy-5-methoxy-benzene carbonylate in the presence of active copper or coupling agent Ni(PPh3)2Cl/Zn/NaH in good yield, and then it was converted to 4,4' -dimethoxy-5,6,5' ,6' -dimethenedioxy-biphenyl-2-alkyloxycarbonyl-2' -carboxylic acid. The compounds have been further modified by substituted N-benzyl piperazines to afford corresponding novel biphenyls. The structure of these new compounds was confirmed by 1H NMR, IR and ESI-MS.
Activity, against simian immunodeficiency virus, of some novel biphenyl compounds, was tested in vitro. All of those showed activity of anti-virus. At the compounds concentration of 7.8 ug/mL, compounds, 2-24, 2-30, 2-42, showed 47.4,
38.0, 32.3% reduction in antigen, respectively. Among the three compounds, compound 2-24 possesses the more potent anti-HIV activity. It is noticeable that compound 2-20 exhibit 44.7% reduction in antigen at concentration of 2.0 u.g/mL(2.9uM).
The second type of novel compounds, 4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-2-(2-(4-substituted-benzyl~piperazine-l-yl-)-acetoxymethyl)-2'-methoxycarbonyl-biphenyl, were synthesized. The key intermediate, 4,4'-dimethoxy-5,6,5',6'-dimethenedioxyl-2-hydroxymethyl-2'-methoxycarbonyl-biphenyl, was prepared by two methods. One method was selective reduction of methyl-4,4'-dimethoxy-5,6,5', 6'-dimethenedioxy-biphenyl-2,2'-dicarbonylate by NaBH4-I2. The second was intramolecular coupling of 2-bromo-5-methoxy-3,4- methenedioxybenzyl 2-bromo-5-methoxy-3,4-methenedioxybenzoate in the presence of activated copper or CuTC. The structure of the aimed compounds was confirmed by means of 1H NMR, 13C NMR, HSQC, HMBC, NOESY and ESI-MS.
(S)-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-2,2'-di-(4(S)-methyl-oxazoline-l)-biphenyl was synthesized through asymmetric Ullmann coupling reaction or asymmetric Ullmann-type coupling reaction in the presence of Ni(PPh3)2Cl/Zn/NaH.
In the thesis, it was found for the first time that the arylbromide with ortho metheneoxy and chiral oxazoline group can couple to give corresponding biphenyl in the presence of Ni(PPh3)2Cl/Zn/NaH. In the asymmetric Ullmann-type, It was noticeable that which was excessive among the biphenyl with S or R configuration was dependent on ratio of Ni(PPh3)2Cl2 to aryl bromide. 0.5 equiv Ni(PPh3)2Cl2 gave
excessive R and 1 equiv or more Ni(PPh3)2Cl2 afforded excessive S. The different stereoselectivity should reflect two kinds of coupling mechanism, intermolecular and intramolecular coupling of Ni-complex intermediate.
we have also found another efficacious method to prepare (S)-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-2,2'-di-[4(S)-methyl-oxazoline-l]-biph enyl through configuration transform of (R/S)-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-2,2'-di-(4(S)-methyl-oxazoline-l)-bi-biphenyl in excellent yield promoted by interaction between chiral oxazolines moiety of biphenyl and Cu(I). (S)-dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-biphen-yl-2,2'-dicarboxylate was prepared from (S)-2,2'-dioxazoline biphenyl isomer conveniently.
At last, the mechanism of asymmetric Ullmann coupling, asymmetric Ullmann-t
引文
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2. MacRae, W. D.; Hudason, J. B.; Towers, G. H. N. The antivirsol action of lignans. Planta Med. 1989, 55, 531
3．谢晶曦，中国药学年签，1985，p52
4．钮心懿，王维君，边振甲等，药学学报，1983，18，416
5. Hikino, H.; Kiso, Y. Ikeya. Y. et al. Antihepatotoxic actions of lignana from schisandrin chinensis fruit. Planta Med. 1984, 50, 213
6. Kupchan S M, Britton R W, Zigler M F, et al. J. Am. Chem. Soc. 1973, 95, 1335
7. Hekino H., planta Med. 1984, 50(3), 213
8. IP, S. R; CHE, C. T.; KO, K. M. Acta Pharmacologica Sinica, 1998, 19(4), 313-316.
9. Kiso, Y.; Planta Med. 1985, 51(4), 331
10．刘耕陶，生理科学进展，1988，19(3)，197
11. Mizoguchi, Y., Planta Med. 1991, 57, 11
12. Mizoguchi, Y., Planta Med. 1991, 57, 1320
13. CA, 1993, 118:225165j
14. Kuo, Y. H.; Chem. Pharm. Bull., 1999. 47(7). 1047
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22．刘志毅，刘耕陶，张世馥，中华医学杂志．1995．75(11)．676-678．
23 郭瑞云，常俊标，陈荣峰，范小玲，谢晶曦，药学学报，1999，36，439-441．)
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44. Hovorka, M.; Scigel, R.; Gunterová, J.; Tichy, M.; Závada, J. Tetrahedron 1992, 48, 9503
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20. Liu, J. S.; Li, L. Kadsulignans, L. N. Phytochemistry, 1995, 38(1), 241-246.
21. Chen D. F.; Zhang, S. X.; Kozuka, M.; Sun, Q. Z.; Feng, J.; Wang, Q, Mukainaka T, Nobukuni Y, Tokuda H, Nishino H, Wang HK, Morris-Natschk.; SL, Lee, K. H. J. Nat. Prod. 2002, 65(9),1242-1245.
22．刘志毅，刘耕陶，张世馥，中华医学杂志．1995．75(11)．676-678．
23 郭瑞云，常俊标，陈荣峰，范小玲，谢晶曦，药学学报，1999，36，439-441．)
24. Ullmann, F.; Bielecki, J. Chem. Ber. 1901, 34, 2174.
25. Lindlay, J.; Mason, T. J.; Lorimer, J. R Ultrasonics 1987, 25, 45; Chem. Abstr. 1987, 107, 96106.
27. Lee Kuo-Hsiung; Kashiwada Yoshiki; Xie Lan; Cosentino Louis M.; Manak Mark; Xie Jing-Xi; Cheng Yung-Chi; Kilkulskie Robert, USP 5 612 341, 1997
28. Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869
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34 Piers, E.; Yee, J. G. K.; Gladstone, P. L. Org. Lett. 2000, 2, 481.
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37. Iyoda, M.; Kondo, T.; Nakao, K.; Hara, K.; Kuwatani, Y.; Yoshida, M.; Matsuyama, H. Org. Lett. 2000, 2, 2081
38 Harada, G.; Yoshida, M.; Iyoda, M. Chem. Lett. 2000, 160
39. Lipshutz, B. H.; Kayser, F.; Liu, Z.-P. Angew. Chem., Int. Ed. Engl. 1994, 33, 1842.
40. Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503.
41. Smrcina, M.; Lorenc, M.; Hanus, V.; Kocovsky, P. Synlett 1991, 231.
42. Smrcina, M.; Lorenc, M.; Hanus, V.; Sedmera, P.; Kocovsky, P. J. Org. Chem. 1992, 57, 1917.
43. Smrcina, M.; Poláková, J.; Vyskocil, S.; Kocovsky, P. J. Org. Chem. 1993, 58, 4534.
44. Hovorka, M.; Scigel, R.; Gunterová, J.; Tichy, M.; Závada, J. Tetrahedron 1992, 48, 9503
45. Hovorka, M.; Závada, J. Tetrahedron 1992, 48, 9517.
46. Smrcina, M.; Vyskocil, S.; Maca, B.; Polasek, M.; Claxton, T. A.; Abbott, A. P.; Kocovsky, P. J. Org. Chem. 1994, 59, 2156.
47. Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983.
48. Nakajima, M.; Kanayama, K.; Miyoshi, I.; Hashimoto, S.-I. Tetrahedron Lett. 1995, 36, 9519.
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50. Sakamoto, T.; Yonehara, H.; Pac, C. J Org. Chem. 1994, 59, 6859.
51. Sakamoto, T.; Yonehara, H.; Pac, C. J. Org. Chem. 1997, 62, 3194.
52. Lakshmi Kantam, M.; Lakshmi Santhi, P. Synth. Commun. 1996, 26, 3075.
53. Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374
54. Kumada, M. Pure Appl. Chem. 1980, 52, 669.
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59. Tiecco, M.; Testaferri, L.; Tingoli, M.; Chainelli, D.; Montanucci, M. Synthesis 1984, 736.
60. Trecourt, F.; Mallet, M.; Mongin, O.; Gervais, B.; Quéguiner, G. Tetrahedron 1993, 49, 8373.
61. Janiak, C.; Deblon, S.; Uehlin, S. Synthesis 1999, 959.
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