An effective method for the synthesis of 13C-labeled polyprenylhydroxybenzoic acids

Synthesis

Volumn , Issue 6, 2005, Pages 1019-1027

  Lang, Martin ^a,b   Steglich, Wolfgang ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b 4SC AG   (Germany)

Author keywords

Allylations; Copper; Coupling; Grignard reactions; Organometallic reagents

Indexed keywords

CATALYSIS; COPPER; LOW TEMPERATURE EFFECTS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CROSS-COUPLING; DEPROTECTION; GERANYLGERANYL BROMIDE; GRIGNARD REAGENTS;

CARBOXYLIC ACIDS;

BROMINE DERIVATIVE; CARBON 13; COPPER; HYDROXYBENZOIC ACID DERIVATIVE; IODINE; MAGNESIUM;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; DEPROTECTION REACTION; GRIGNARD REACTION; LOW TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 17744388396     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-861863     Document Type: Article

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74. For 3-geranyl-4-hydroxybenzoic acid: (a) Yazaki, K.; Fukui, H.; Tabata, M. Chem. Pharm. Bull. 1986, 34, 2290. (b) Seeram, N. P.; Jacobs, H.; McLean, S.; Reynolds, W. F. Phytochemistry 1996, 43, 863. (c) Baldoqui, D. C.; Kato, M. J.; Cavalheiro, A. J.; Bolzani, V. da S.; Young, M. C. M.; Furlan, M. Phytochemistry 1999, 51, 899. For 3-farnesyl-4-hydroxybenzoic acid: (d) Ampofo, S. A.; Roussis, V.; Wiemer, D. F. Phytochemistry 1987, 26, 2367. (e) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1988, 51, 370. For 3-geranylgeranyl-4- hydroxybenzoic acid: (f) Cimino, G.; De Stefano, S.; Minale, L. Experientia 1972, 28, 1401. (g) Lütke-Brinkhaus, F.; Liedvogel, B.; Kleinig, H. Eur. J. Biochem. 1984, 537. (h) Perez Baz, J.; Canedo, L. M.; Tapiolas, D. J. Nat. Prod. 1996, 59, 960. (i) Kang, H.-C.; Yun, B.-S.; Yu, H.; Yoo, I.-D. Sanop Misaengmul Hakhoechi 2001, 29, 149; Chem. Abstr. 2002, 136, 275806. For 3-geranylgeranyl-4,5-dihydroxybenzoic acid and 2-geranylgeranyl-3,4- dihydroxybenzoic acid: (j) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 614. (k) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 891.
75. For 3-geranyl-4-hydroxybenzoic acid: (a) Yazaki, K.; Fukui, H.; Tabata, M. Chem. Pharm. Bull. 1986, 34, 2290. (b) Seeram, N. P.; Jacobs, H.; McLean, S.; Reynolds, W. F. Phytochemistry 1996, 43, 863. (c) Baldoqui, D. C.; Kato, M. J.; Cavalheiro, A. J.; Bolzani, V. da S.; Young, M. C. M.; Furlan, M. Phytochemistry 1999, 51, 899. For 3-farnesyl-4-hydroxybenzoic acid: (d) Ampofo, S. A.; Roussis, V.; Wiemer, D. F. Phytochemistry 1987, 26, 2367. (e) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1988, 51, 370. For 3-geranylgeranyl-4- hydroxybenzoic acid: (f) Cimino, G.; De Stefano, S.; Minale, L. Experientia 1972, 28, 1401. (g) Lütke-Brinkhaus, F.; Liedvogel, B.; Kleinig, H. Eur. J. Biochem. 1984, 537. (h) Perez Baz, J.; Canedo, L. M.; Tapiolas, D. J. Nat. Prod. 1996, 59, 960. (i) Kang, H.-C.; Yun, B.-S.; Yu, H.; Yoo, I.-D. Sanop Misaengmul Hakhoechi 2001, 29, 149; Chem. Abstr. 2002, 136, 275806. For 3-geranylgeranyl-4,5-dihydroxybenzoic acid and 2-geranylgeranyl-3,4- dihydroxybenzoic acid: (j) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 614. (k) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 891.
76. For 3-geranyl-4-hydroxybenzoic acid: (a) Yazaki, K.; Fukui, H.; Tabata, M. Chem. Pharm. Bull. 1986, 34, 2290. (b) Seeram, N. P.; Jacobs, H.; McLean, S.; Reynolds, W. F. Phytochemistry 1996, 43, 863. (c) Baldoqui, D. C.; Kato, M. J.; Cavalheiro, A. J.; Bolzani, V. da S.; Young, M. C. M.; Furlan, M. Phytochemistry 1999, 51, 899. For 3-farnesyl-4-hydroxybenzoic acid: (d) Ampofo, S. A.; Roussis, V.; Wiemer, D. F. Phytochemistry 1987, 26, 2367. (e) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1988, 51, 370. For 3-geranylgeranyl-4- hydroxybenzoic acid: (f) Cimino, G.; De Stefano, S.; Minale, L. Experientia 1972, 28, 1401. (g) Lütke-Brinkhaus, F.; Liedvogel, B.; Kleinig, H. Eur. J. Biochem. 1984, 537. (h) Perez Baz, J.; Canedo, L. M.; Tapiolas, D. J. Nat. Prod. 1996, 59, 960. (i) Kang, H.-C.; Yun, B.-S.; Yu, H.; Yoo, I.-D. Sanop Misaengmul Hakhoechi 2001, 29, 149; Chem. Abstr. 2002, 136, 275806. For 3-geranylgeranyl-4,5-dihydroxybenzoic acid and 2-geranylgeranyl-3,4- dihydroxybenzoic acid: (j) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 614. (k) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 891.
77. For 3-geranyl-4-hydroxybenzoic acid: (a) Yazaki, K.; Fukui, H.; Tabata, M. Chem. Pharm. Bull. 1986, 34, 2290. (b) Seeram, N. P.; Jacobs, H.; McLean, S.; Reynolds, W. F. Phytochemistry 1996, 43, 863. (c) Baldoqui, D. C.; Kato, M. J.; Cavalheiro, A. J.; Bolzani, V. da S.; Young, M. C. M.; Furlan, M. Phytochemistry 1999, 51, 899. For 3-farnesyl-4-hydroxybenzoic acid: (d) Ampofo, S. A.; Roussis, V.; Wiemer, D. F. Phytochemistry 1987, 26, 2367. (e) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1988, 51, 370. For 3-geranylgeranyl-4- hydroxybenzoic acid: (f) Cimino, G.; De Stefano, S.; Minale, L. Experientia 1972, 28, 1401. (g) Lütke-Brinkhaus, F.; Liedvogel, B.; Kleinig, H. Eur. J. Biochem. 1984, 537. (h) Perez Baz, J.; Canedo, L. M.; Tapiolas, D. J. Nat. Prod. 1996, 59, 960. (i) Kang, H.-C.; Yun, B.-S.; Yu, H.; Yoo, I.-D. Sanop Misaengmul Hakhoechi 2001, 29, 149; Chem. Abstr. 2002, 136, 275806. For 3-geranylgeranyl-4,5-dihydroxybenzoic acid and 2-geranylgeranyl-3,4- dihydroxybenzoic acid: (j) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 614. (k) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 891.
78. For 3-geranyl-4-hydroxybenzoic acid: (a) Yazaki, K.; Fukui, H.; Tabata, M. Chem. Pharm. Bull. 1986, 34, 2290. (b) Seeram, N. P.; Jacobs, H.; McLean, S.; Reynolds, W. F. Phytochemistry 1996, 43, 863. (c) Baldoqui, D. C.; Kato, M. J.; Cavalheiro, A. J.; Bolzani, V. da S.; Young, M. C. M.; Furlan, M. Phytochemistry 1999, 51, 899. For 3-farnesyl-4-hydroxybenzoic acid: (d) Ampofo, S. A.; Roussis, V.; Wiemer, D. F. Phytochemistry 1987, 26, 2367. (e) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1988, 51, 370. For 3-geranylgeranyl-4- hydroxybenzoic acid: (f) Cimino, G.; De Stefano, S.; Minale, L. Experientia 1972, 28, 1401. (g) Lütke-Brinkhaus, F.; Liedvogel, B.; Kleinig, H. Eur. J. Biochem. 1984, 537. (h) Perez Baz, J.; Canedo, L. M.; Tapiolas, D. J. Nat. Prod. 1996, 59, 960. (i) Kang, H.-C.; Yun, B.-S.; Yu, H.; Yoo, I.-D. Sanop Misaengmul Hakhoechi 2001, 29, 149; Chem. Abstr. 2002, 136, 275806. For 3-geranylgeranyl-4,5-dihydroxybenzoic acid and 2-geranylgeranyl-3,4- dihydroxybenzoic acid: (j) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 614. (k) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 891.
79. For 3-geranyl-4-hydroxybenzoic acid: (a) Yazaki, K.; Fukui, H.; Tabata, M. Chem. Pharm. Bull. 1986, 34, 2290. (b) Seeram, N. P.; Jacobs, H.; McLean, S.; Reynolds, W. F. Phytochemistry 1996, 43, 863. (c) Baldoqui, D. C.; Kato, M. J.; Cavalheiro, A. J.; Bolzani, V. da S.; Young, M. C. M.; Furlan, M. Phytochemistry 1999, 51, 899. For 3-farnesyl-4-hydroxybenzoic acid: (d) Ampofo, S. A.; Roussis, V.; Wiemer, D. F. Phytochemistry 1987, 26, 2367. (e) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1988, 51, 370. For 3-geranylgeranyl-4- hydroxybenzoic acid: (f) Cimino, G.; De Stefano, S.; Minale, L. Experientia 1972, 28, 1401. (g) Lütke-Brinkhaus, F.; Liedvogel, B.; Kleinig, H. Eur. J. Biochem. 1984, 537. (h) Perez Baz, J.; Canedo, L. M.; Tapiolas, D. J. Nat. Prod. 1996, 59, 960. (i) Kang, H.-C.; Yun, B.-S.; Yu, H.; Yoo, I.-D. Sanop Misaengmul Hakhoechi 2001, 29, 149; Chem. Abstr. 2002, 136, 275806. For 3-geranylgeranyl-4,5-dihydroxybenzoic acid and 2-geranylgeranyl-3,4- dihydroxybenzoic acid: (j) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 614. (k) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 891.
80. For 3-geranyl-4-hydroxybenzoic acid: (a) Yazaki, K.; Fukui, H.; Tabata, M. Chem. Pharm. Bull. 1986, 34, 2290. (b) Seeram, N. P.; Jacobs, H.; McLean, S.; Reynolds, W. F. Phytochemistry 1996, 43, 863. (c) Baldoqui, D. C.; Kato, M. J.; Cavalheiro, A. J.; Bolzani, V. da S.; Young, M. C. M.; Furlan, M. Phytochemistry 1999, 51, 899. For 3-farnesyl-4-hydroxybenzoic acid: (d) Ampofo, S. A.; Roussis, V.; Wiemer, D. F. Phytochemistry 1987, 26, 2367. (e) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1988, 51, 370. For 3-geranylgeranyl-4- hydroxybenzoic acid: (f) Cimino, G.; De Stefano, S.; Minale, L. Experientia 1972, 28, 1401. (g) Lütke-Brinkhaus, F.; Liedvogel, B.; Kleinig, H. Eur. J. Biochem. 1984, 537. (h) Perez Baz, J.; Canedo, L. M.; Tapiolas, D. J. Nat. Prod. 1996, 59, 960. (i) Kang, H.-C.; Yun, B.-S.; Yu, H.; Yoo, I.-D. Sanop Misaengmul Hakhoechi 2001, 29, 149; Chem. Abstr. 2002, 136, 275806. For 3-geranylgeranyl-4,5-dihydroxybenzoic acid and 2-geranylgeranyl-3,4- dihydroxybenzoic acid: (j) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 614. (k) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 891.
81. For 3-geranyl-4-hydroxybenzoic acid: (a) Yazaki, K.; Fukui, H.; Tabata, M. Chem. Pharm. Bull. 1986, 34, 2290. (b) Seeram, N. P.; Jacobs, H.; McLean, S.; Reynolds, W. F. Phytochemistry 1996, 43, 863. (c) Baldoqui, D. C.; Kato, M. J.; Cavalheiro, A. J.; Bolzani, V. da S.; Young, M. C. M.; Furlan, M. Phytochemistry 1999, 51, 899. For 3-farnesyl-4-hydroxybenzoic acid: (d) Ampofo, S. A.; Roussis, V.; Wiemer, D. F. Phytochemistry 1987, 26, 2367. (e) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1988, 51, 370. For 3-geranylgeranyl-4- hydroxybenzoic acid: (f) Cimino, G.; De Stefano, S.; Minale, L. Experientia 1972, 28, 1401. (g) Lütke-Brinkhaus, F.; Liedvogel, B.; Kleinig, H. Eur. J. Biochem. 1984, 537. (h) Perez Baz, J.; Canedo, L. M.; Tapiolas, D. J. Nat. Prod. 1996, 59, 960. (i) Kang, H.-C.; Yun, B.-S.; Yu, H.; Yoo, I.-D. Sanop Misaengmul Hakhoechi 2001, 29, 149; Chem. Abstr. 2002, 136, 275806. For 3-geranylgeranyl-4,5-dihydroxybenzoic acid and 2-geranylgeranyl-3,4- dihydroxybenzoic acid: (j) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 614. (k) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 891.
82. For 3-geranyl-4-hydroxybenzoic acid: (a) Yazaki, K.; Fukui, H.; Tabata, M. Chem. Pharm. Bull. 1986, 34, 2290. (b) Seeram, N. P.; Jacobs, H.; McLean, S.; Reynolds, W. F. Phytochemistry 1996, 43, 863. (c) Baldoqui, D. C.; Kato, M. J.; Cavalheiro, A. J.; Bolzani, V. da S.; Young, M. C. M.; Furlan, M. Phytochemistry 1999, 51, 899. For 3-farnesyl-4-hydroxybenzoic acid: (d) Ampofo, S. A.; Roussis, V.; Wiemer, D. F. Phytochemistry 1987, 26, 2367. (e) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1988, 51, 370. For 3-geranylgeranyl-4- hydroxybenzoic acid: (f) Cimino, G.; De Stefano, S.; Minale, L. Experientia 1972, 28, 1401. (g) Lütke-Brinkhaus, F.; Liedvogel, B.; Kleinig, H. Eur. J. Biochem. 1984, 537. (h) Perez Baz, J.; Canedo, L. M.; Tapiolas, D. J. Nat. Prod. 1996, 59, 960. (i) Kang, H.-C.; Yun, B.-S.; Yu, H.; Yoo, I.-D. Sanop Misaengmul Hakhoechi 2001, 29, 149; Chem. Abstr. 2002, 136, 275806. For 3-geranylgeranyl-4,5-dihydroxybenzoic acid and 2-geranylgeranyl-3,4- dihydroxybenzoic acid: (j) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 614. (k) Maxwell, A.; Rampersad, D. J. Nat. Prod. 1989, 52, 891.
83. (a) Kofron, W. G.; Baclawski, L. M. J. Org. Chem. 1976, 41, 1879.
84. (b) 4-Biphenylmethanol may also be used, see: Juaristi, E.; Martínez-Richa, A.; García-Rivera, A.; Cruz-Sánchez, J. S. J. Org. Chem. 1983, 48, 2603.
85. Methyl 4-hydroxy-3,5-diiodobenzoate was separated from 1 by flash chromatography. Non-iodinated material could be removed neither from 1 nor from 2. Thus, a mixture of 2 and methyl 4-(methoxymethoxy)benzoate was employed in the cross coupling reactions.
86. Edwards, R. L.; Wilson, D. V. J. Chem. Soc. 1961, 5003.
87. Impurity: 2-iodo-4,5-bis(methoxymethoxy)benzaldehyde.
88. Chaudhary, S. K.; Hernandez, O. Tetrahedron Lett. 1979, 20, 99.
89. Determination of the concentration: In a dried and argon-flushed Schlenk flask with gas inlet and rubber septum, an exactly known amount of menthol (approx. 0.8 mmol) and a few mg of 1,10-phenanthroline were dissolved in anhyd THF (2.5 mL). The i-PrMgBr solution was added dropwise until blue color appeared. See: Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 9, 165.
90. IR data of the corresponding unlabeled compound.