Synthesis of 6-(poly)prenyl-substituted polyprenols and their phosphates

Tetrahedron

Volumn 55, Issue 9, 1999, Pages 2591-2608

  Nagano, Hajime ^a   Nakanishi, Eiyu ^a   Takajo, Saho ^a   Sakuma, Masako ^a   Kudo, Kaori ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOACETIC ACID DERIVATIVE; ACID; BROMINE DERIVATIVE; DISODIUM HYDROGEN PHOSPHATE; GEFARNATE; GERANIOL; ISOPRENOID PHOSPHATE; KETONE DERIVATIVE; POLYPRENOIC ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DESICCATION; PRENYLATION; PRIORITY JOURNAL; REDUCTION; SYNTHESIS;

EID: 0033605188     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00057-5     Document Type: Article

References (52)

1. (a) Volkman, J. K.; Farrington, J. W.; Gagosian. R. B.; Wakeham, S. G. "Advances in Organic Geochemistry 1981," ed by M. Bjoroy, Wiley, Chichester, 1983, 228-240. (b) Robson, J. N.; Rowland, S. J. Nature 1986, 324, 561. (c) Hird, S. J.; Evens, R.; Rowland, S. J. Mar. Chem. 1992, 37, 117. (d) Belt, S. T.; Cooke, D. A.; Hird, S. J.; Rowland, S. J. Chem. Soc., Chem. Commun. 1994, 2077. (e) Hoefs, M. J. L.; Damsté, J. S. S.; de Leeuw, J. W. Org. Geochem. 1995, 23, 263. (f) Huang, Y.; Murray, M.; Eglinton, G; Metzger, P. Tetrahedron Lett. 1995, 36, 5973. (g) Rospondek, M. J.; Koster, J.; Sinninghe Damste, J. S. Org. Geochem. 1997, 26, 295.
2. (a) Volkman, J. K.; Farrington, J. W.; Gagosian. R. B.; Wakeham, S. G. "Advances in Organic Geochemistry 1981," ed by M. Bjoroy, Wiley, Chichester, 1983, 228-240. (b) Robson, J. N.; Rowland, S. J. Nature 1986, 324, 561. (c) Hird, S. J.; Evens, R.; Rowland, S. J. Mar. Chem. 1992, 37, 117. (d) Belt, S. T.; Cooke, D. A.; Hird, S. J.; Rowland, S. J. Chem. Soc., Chem. Commun. 1994, 2077. (e) Hoefs, M. J. L.; Damsté, J. S. S.; de Leeuw, J. W. Org. Geochem. 1995, 23, 263. (f) Huang, Y.; Murray, M.; Eglinton, G; Metzger, P. Tetrahedron Lett. 1995, 36, 5973. (g) Rospondek, M. J.; Koster, J.; Sinninghe Damste, J. S. Org. Geochem. 1997, 26, 295.
3. (a) Volkman, J. K.; Farrington, J. W.; Gagosian. R. B.; Wakeham, S. G. "Advances in Organic Geochemistry 1981," ed by M. Bjoroy, Wiley, Chichester, 1983, 228-240. (b) Robson, J. N.; Rowland, S. J. Nature 1986, 324, 561. (c) Hird, S. J.; Evens, R.; Rowland, S. J. Mar. Chem. 1992, 37, 117. (d) Belt, S. T.; Cooke, D. A.; Hird, S. J.; Rowland, S. J. Chem. Soc., Chem. Commun. 1994, 2077. (e) Hoefs, M. J. L.; Damsté, J. S. S.; de Leeuw, J. W. Org. Geochem. 1995, 23, 263. (f) Huang, Y.; Murray, M.; Eglinton, G; Metzger, P. Tetrahedron Lett. 1995, 36, 5973. (g) Rospondek, M. J.; Koster, J.; Sinninghe Damste, J. S. Org. Geochem. 1997, 26, 295.
4. (a) Volkman, J. K.; Farrington, J. W.; Gagosian. R. B.; Wakeham, S. G. "Advances in Organic Geochemistry 1981," ed by M. Bjoroy, Wiley, Chichester, 1983, 228-240. (b) Robson, J. N.; Rowland, S. J. Nature 1986, 324, 561. (c) Hird, S. J.; Evens, R.; Rowland, S. J. Mar. Chem. 1992, 37, 117. (d) Belt, S. T.; Cooke, D. A.; Hird, S. J.; Rowland, S. J. Chem. Soc., Chem. Commun. 1994, 2077. (e) Hoefs, M. J. L.; Damsté, J. S. S.; de Leeuw, J. W. Org. Geochem. 1995, 23, 263. (f) Huang, Y.; Murray, M.; Eglinton, G; Metzger, P. Tetrahedron Lett. 1995, 36, 5973. (g) Rospondek, M. J.; Koster, J.; Sinninghe Damste, J. S. Org. Geochem. 1997, 26, 295.
5. (a) Volkman, J. K.; Farrington, J. W.; Gagosian. R. B.; Wakeham, S. G. "Advances in Organic Geochemistry 1981," ed by M. Bjoroy, Wiley, Chichester, 1983, 228-240. (b) Robson, J. N.; Rowland, S. J. Nature 1986, 324, 561. (c) Hird, S. J.; Evens, R.; Rowland, S. J. Mar. Chem. 1992, 37, 117. (d) Belt, S. T.; Cooke, D. A.; Hird, S. J.; Rowland, S. J. Chem. Soc., Chem. Commun. 1994, 2077. (e) Hoefs, M. J. L.; Damsté, J. S. S.; de Leeuw, J. W. Org. Geochem. 1995, 23, 263. (f) Huang, Y.; Murray, M.; Eglinton, G; Metzger, P. Tetrahedron Lett. 1995, 36, 5973. (g) Rospondek, M. J.; Koster, J.; Sinninghe Damste, J. S. Org. Geochem. 1997, 26, 295.
6. (a) Volkman, J. K.; Farrington, J. W.; Gagosian. R. B.; Wakeham, S. G. "Advances in Organic Geochemistry 1981," ed by M. Bjoroy, Wiley, Chichester, 1983, 228-240. (b) Robson, J. N.; Rowland, S. J. Nature 1986, 324, 561. (c) Hird, S. J.; Evens, R.; Rowland, S. J. Mar. Chem. 1992, 37, 117. (d) Belt, S. T.; Cooke, D. A.; Hird, S. J.; Rowland, S. J. Chem. Soc., Chem. Commun. 1994, 2077. (e) Hoefs, M. J. L.; Damsté, J. S. S.; de Leeuw, J. W. Org. Geochem. 1995, 23, 263. (f) Huang, Y.; Murray, M.; Eglinton, G; Metzger, P. Tetrahedron Lett. 1995, 36, 5973. (g) Rospondek, M. J.; Koster, J.; Sinninghe Damste, J. S. Org. Geochem. 1997, 26, 295.
7. (a) Volkman, J. K.; Farrington, J. W.; Gagosian. R. B.; Wakeham, S. G. "Advances in Organic Geochemistry 1981," ed by M. Bjoroy, Wiley, Chichester, 1983, 228-240. (b) Robson, J. N.; Rowland, S. J. Nature 1986, 324, 561. (c) Hird, S. J.; Evens, R.; Rowland, S. J. Mar. Chem. 1992, 37, 117. (d) Belt, S. T.; Cooke, D. A.; Hird, S. J.; Rowland, S. J. Chem. Soc., Chem. Commun. 1994, 2077. (e) Hoefs, M. J. L.; Damsté, J. S. S.; de Leeuw, J. W. Org. Geochem. 1995, 23, 263. (f) Huang, Y.; Murray, M.; Eglinton, G; Metzger, P. Tetrahedron Lett. 1995, 36, 5973. (g) Rospondek, M. J.; Koster, J.; Sinninghe Damste, J. S. Org. Geochem. 1997, 26, 295.
8. (a) Ourisson, G.; Nakatani, Y. Chem. Biol. 1994, 1, 11. (b) Ourisson, G.; Nakatani, Y. C. R. Acad. Sci. Paris 1996, 322, Série IIb, 323.
9. (a) Ourisson, G.; Nakatani, Y. Chem. Biol. 1994, 1, 11. (b) Ourisson, G.; Nakatani, Y. C. R. Acad. Sci. Paris 1996, 322, Série IIb, 323.
10. (a) Plobeck, N.; Eifler, S.; Brisson, A.; Nakatani, Y.; Ourisson, G. Tetrahedron Lett. 1992, 33, 5249. (b) Pozzi, G.; Birault, V.; Werner, B.; Dannenmuller, O.; Nakatani, Y.; Ourisson, G.; Terakawa, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 177.
11. (a) Plobeck, N.; Eifler, S.; Brisson, A.; Nakatani, Y.; Ourisson, G. Tetrahedron Lett. 1992, 33, 5249. (b) Pozzi, G.; Birault, V.; Werner, B.; Dannenmuller, O.; Nakatani, Y.; Ourisson, G.; Terakawa, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 177.
12. Highly branched isoprenoid alkenes and alkanes have been isolated from diatomaceous algae, (a) Rowland, S. J.; Robson, J. N. Mar. Environ. Res. 1990, 30, 191. (b) Summons, R. E.; Barrow, R. A.; Capon, R. J.; Hope, J. M.; Stranger, C. Aust. J. Chem. 1993, 46, 907. (c) Volkman, J. K.; Barrett, S. M.; Dunstan, G. A. Org. Geochem. 1994, 21, 407. (d) Belt, S. T.; Cooke, D. A.; Robert, J.-M.; Rowland, S. Tetrahedron Lett. 1996, 37, 4755. (e) Wraige, E. J.; Belt, S. T.; Lewis, C. A.; Cooke, D. A.; Robert, J. M.; Masse, G.; Rowland, S. J. Org. Geochem. 1997, 27, 497. see also, (a) Rowland, S. J.; Yon, D. A.; Lewis, C. A.; Maxwell, J. R. Org. Geochem. 1985, 8, 207. (b) Porte, C.; Barceló, D.; Tavares, T. M.; Rocha, V. C.; Albaigés, J. Arch. Environ. Contam. Toxicol. 1990, 19, 263.
13. Highly branched isoprenoid alkenes and alkanes have been isolated from diatomaceous algae, (a) Rowland, S. J.; Robson, J. N. Mar. Environ. Res. 1990, 30, 191. (b) Summons, R. E.; Barrow, R. A.; Capon, R. J.; Hope, J. M.; Stranger, C. Aust. J. Chem. 1993, 46, 907. (c) Volkman, J. K.; Barrett, S. M.; Dunstan, G. A. Org. Geochem. 1994, 21, 407. (d) Belt, S. T.; Cooke, D. A.; Robert, J.-M.; Rowland, S. Tetrahedron Lett. 1996, 37, 4755. (e) Wraige, E. J.; Belt, S. T.; Lewis, C. A.; Cooke, D. A.; Robert, J. M.; Masse, G.; Rowland, S. J. Org. Geochem. 1997, 27, 497. see also, (a) Rowland, S. J.; Yon, D. A.; Lewis, C. A.; Maxwell, J. R. Org. Geochem. 1985, 8, 207. (b) Porte, C.; Barceló, D.; Tavares, T. M.; Rocha, V. C.; Albaigés, J. Arch. Environ. Contam. Toxicol. 1990, 19, 263.
14. Highly branched isoprenoid alkenes and alkanes have been isolated from diatomaceous algae, (a) Rowland, S. J.; Robson, J. N. Mar. Environ. Res. 1990, 30, 191. (b) Summons, R. E.; Barrow, R. A.; Capon, R. J.; Hope, J. M.; Stranger, C. Aust. J. Chem. 1993, 46, 907. (c) Volkman, J. K.; Barrett, S. M.; Dunstan, G. A. Org. Geochem. 1994, 21, 407. (d) Belt, S. T.; Cooke, D. A.; Robert, J.-M.; Rowland, S. Tetrahedron Lett. 1996, 37, 4755. (e) Wraige, E. J.; Belt, S. T.; Lewis, C. A.; Cooke, D. A.; Robert, J. M.; Masse, G.; Rowland, S. J. Org. Geochem. 1997, 27, 497. see also, (a) Rowland, S. J.; Yon, D. A.; Lewis, C. A.; Maxwell, J. R. Org. Geochem. 1985, 8, 207. (b) Porte, C.; Barceló, D.; Tavares, T. M.; Rocha, V. C.; Albaigés, J. Arch. Environ. Contam. Toxicol. 1990, 19, 263.
15. Highly branched isoprenoid alkenes and alkanes have been isolated from diatomaceous algae, (a) Rowland, S. J.; Robson, J. N. Mar. Environ. Res. 1990, 30, 191. (b) Summons, R. E.; Barrow, R. A.; Capon, R. J.; Hope, J. M.; Stranger, C. Aust. J. Chem. 1993, 46, 907. (c) Volkman, J. K.; Barrett, S. M.; Dunstan, G. A. Org. Geochem. 1994, 21, 407. (d) Belt, S. T.; Cooke, D. A.; Robert, J.-M.; Rowland, S. Tetrahedron Lett. 1996, 37, 4755. (e) Wraige, E. J.; Belt, S. T.; Lewis, C. A.; Cooke, D. A.; Robert, J. M.; Masse, G.; Rowland, S. J. Org. Geochem. 1997, 27, 497. see also, (a) Rowland, S. J.; Yon, D. A.; Lewis, C. A.; Maxwell, J. R. Org. Geochem. 1985, 8, 207. (b) Porte, C.; Barceló, D.; Tavares, T. M.; Rocha, V. C.; Albaigés, J. Arch. Environ. Contam. Toxicol. 1990, 19, 263.
16. Highly branched isoprenoid alkenes and alkanes have been isolated from diatomaceous algae, (a) Rowland, S. J.; Robson, J. N. Mar. Environ. Res. 1990, 30, 191. (b) Summons, R. E.; Barrow, R. A.; Capon, R. J.; Hope, J. M.; Stranger, C. Aust. J. Chem. 1993, 46, 907. (c) Volkman, J. K.; Barrett, S. M.; Dunstan, G. A. Org. Geochem. 1994, 21, 407. (d) Belt, S. T.; Cooke, D. A.; Robert, J.-M.; Rowland, S. Tetrahedron Lett. 1996, 37, 4755. (e) Wraige, E. J.; Belt, S. T.; Lewis, C. A.; Cooke, D. A.; Robert, J. M.; Masse, G.; Rowland, S. J. Org. Geochem. 1997, 27, 497. see also, (a) Rowland, S. J.; Yon, D. A.; Lewis, C. A.; Maxwell, J. R. Org. Geochem. 1985, 8, 207. (b) Porte, C.; Barceló, D.; Tavares, T. M.; Rocha, V. C.; Albaigés, J. Arch. Environ. Contam. Toxicol. 1990, 19, 263.
17. Highly branched isoprenoid alkenes and alkanes have been isolated from diatomaceous algae, (a) Rowland, S. J.; Robson, J. N. Mar. Environ. Res. 1990, 30, 191. (b) Summons, R. E.; Barrow, R. A.; Capon, R. J.; Hope, J. M.; Stranger, C. Aust. J. Chem. 1993, 46, 907. (c) Volkman, J. K.; Barrett, S. M.; Dunstan, G. A. Org. Geochem. 1994, 21, 407. (d) Belt, S. T.; Cooke, D. A.; Robert, J.-M.; Rowland, S. Tetrahedron Lett. 1996, 37, 4755. (e) Wraige, E. J.; Belt, S. T.; Lewis, C. A.; Cooke, D. A.; Robert, J. M.; Masse, G.; Rowland, S. J. Org. Geochem. 1997, 27, 497. see also, (a) Rowland, S. J.; Yon, D. A.; Lewis, C. A.; Maxwell, J. R. Org. Geochem. 1985, 8, 207. (b) Porte, C.; Barceló, D.; Tavares, T. M.; Rocha, V. C.; Albaigés, J. Arch. Environ. Contam. Toxicol. 1990, 19, 263.
18. Highly branched isoprenoid alkenes and alkanes have been isolated from diatomaceous algae, (a) Rowland, S. J.; Robson, J. N. Mar. Environ. Res. 1990, 30, 191. (b) Summons, R. E.; Barrow, R. A.; Capon, R. J.; Hope, J. M.; Stranger, C. Aust. J. Chem. 1993, 46, 907. (c) Volkman, J. K.; Barrett, S. M.; Dunstan, G. A. Org. Geochem. 1994, 21, 407. (d) Belt, S. T.; Cooke, D. A.; Robert, J.-M.; Rowland, S. Tetrahedron Lett. 1996, 37, 4755. (e) Wraige, E. J.; Belt, S. T.; Lewis, C. A.; Cooke, D. A.; Robert, J. M.; Masse, G.; Rowland, S. J. Org. Geochem. 1997, 27, 497. see also, (a) Rowland, S. J.; Yon, D. A.; Lewis, C. A.; Maxwell, J. R. Org. Geochem. 1985, 8, 207. (b) Porte, C.; Barceló, D.; Tavares, T. M.; Rocha, V. C.; Albaigés, J. Arch. Environ. Contam. Toxicol. 1990, 19, 263.
19. Highly branched polyprenols and related alcohols have been isolated from higher plants, (a) Lemmich, E. Phytochemistry 1979, 18, 1195. (b) Nagano, H; Tori, M.; Shiota, M; de Pascual Teresa, J. Bull. Chem. Soc. Jpn. 1984, 57, 2971. (c) Bruno, M.; Lamartina, L.; Lentini, F.; Pascual, C.; Savona, G. Tetrahedron Lett. 1984, 25, 4287. (d) Mangoni, L.; Merola, D.; Monaco, P.; Parrilli, M.; Previtera, L. Tetrahedron Lett. 1984, 25, 2597. See also, Porte, C.; Barceló, D.; Tavares, T. M.; Rocha, V. C.; Albaigés, J. Arch. Environ. Contam. Toxicol. 1990, 19, 263. Highly branched polyprenyl acetate, a yellow scale pheromone, has been isolated. Gieselmann, M. J.; Moreno, D. S.; Fargerlund, J.; Tashiro, H.; Roelofs, W. L. J. Chem. Ecol. 1979, 5, 27.
20. Highly branched polyprenols and related alcohols have been isolated from higher plants, (a) Lemmich, E. Phytochemistry 1979, 18, 1195. (b) Nagano, H; Tori, M.; Shiota, M; de Pascual Teresa, J. Bull. Chem. Soc. Jpn. 1984, 57, 2971. (c) Bruno, M.; Lamartina, L.; Lentini, F.; Pascual, C.; Savona, G. Tetrahedron Lett. 1984, 25, 4287. (d) Mangoni, L.; Merola, D.; Monaco, P.; Parrilli, M.; Previtera, L. Tetrahedron Lett. 1984, 25, 2597. See also, Porte, C.; Barceló, D.; Tavares, T. M.; Rocha, V. C.; Albaigés, J. Arch. Environ. Contam. Toxicol. 1990, 19, 263. Highly branched polyprenyl acetate, a yellow scale pheromone, has been isolated. Gieselmann, M. J.; Moreno, D. S.; Fargerlund, J.; Tashiro, H.; Roelofs, W. L. J. Chem. Ecol. 1979, 5, 27.
21. Highly branched polyprenols and related alcohols have been isolated from higher plants, (a) Lemmich, E. Phytochemistry 1979, 18, 1195. (b) Nagano, H; Tori, M.; Shiota, M; de Pascual Teresa, J. Bull. Chem. Soc. Jpn. 1984, 57, 2971. (c) Bruno, M.; Lamartina, L.; Lentini, F.; Pascual, C.; Savona, G. Tetrahedron Lett. 1984, 25, 4287. (d) Mangoni, L.; Merola, D.; Monaco, P.; Parrilli, M.; Previtera, L. Tetrahedron Lett. 1984, 25, 2597. See also, Porte, C.; Barceló, D.; Tavares, T. M.; Rocha, V. C.; Albaigés, J. Arch. Environ. Contam. Toxicol. 1990, 19, 263. Highly branched polyprenyl acetate, a yellow scale pheromone, has been isolated. Gieselmann, M. J.; Moreno, D. S.; Fargerlund, J.; Tashiro, H.; Roelofs, W. L. J. Chem. Ecol. 1979, 5, 27.
22. Highly branched polyprenols and related alcohols have been isolated from higher plants, (a) Lemmich, E. Phytochemistry 1979, 18, 1195. (b) Nagano, H; Tori, M.; Shiota, M; de Pascual Teresa, J. Bull. Chem. Soc. Jpn. 1984, 57, 2971. (c) Bruno, M.; Lamartina, L.; Lentini, F.; Pascual, C.; Savona, G. Tetrahedron Lett. 1984, 25, 4287. (d) Mangoni, L.; Merola, D.; Monaco, P.; Parrilli, M.; Previtera, L. Tetrahedron Lett. 1984, 25, 2597. See also, Porte, C.; Barceló, D.; Tavares, T. M.; Rocha, V. C.; Albaigés, J. Arch. Environ. Contam. Toxicol. 1990, 19, 263. Highly branched polyprenyl acetate, a yellow scale pheromone, has been isolated. Gieselmann, M. J.; Moreno, D. S.; Fargerlund, J.; Tashiro, H.; Roelofs, W. L. J. Chem. Ecol. 1979, 5, 27.
23. Highly branched polyprenols and related alcohols have been isolated from higher plants, (a) Lemmich, E. Phytochemistry 1979, 18, 1195. (b) Nagano, H; Tori, M.; Shiota, M; de Pascual Teresa, J. Bull. Chem. Soc. Jpn. 1984, 57, 2971. (c) Bruno, M.; Lamartina, L.; Lentini, F.; Pascual, C.; Savona, G. Tetrahedron Lett. 1984, 25, 4287. (d) Mangoni, L.; Merola, D.; Monaco, P.; Parrilli, M.; Previtera, L. Tetrahedron Lett. 1984, 25, 2597. See also, Porte, C.; Barceló, D.; Tavares, T. M.; Rocha, V. C.; Albaigés, J. Arch. Environ. Contam. Toxicol. 1990, 19, 263. Highly branched polyprenyl acetate, a yellow scale pheromone, has been isolated. Gieselmann, M. J.; Moreno, D. S.; Fargerlund, J.; Tashiro, H.; Roelofs, W. L. J. Chem. Ecol. 1979, 5, 27.
24. Highly branched polyprenols and related alcohols have been isolated from higher plants, (a) Lemmich, E. Phytochemistry 1979, 18, 1195. (b) Nagano, H; Tori, M.; Shiota, M; de Pascual Teresa, J. Bull. Chem. Soc. Jpn. 1984, 57, 2971. (c) Bruno, M.; Lamartina, L.; Lentini, F.; Pascual, C.; Savona, G. Tetrahedron Lett. 1984, 25, 4287. (d) Mangoni, L.; Merola, D.; Monaco, P.; Parrilli, M.; Previtera, L. Tetrahedron Lett. 1984, 25, 2597. See also, Porte, C.; Barceló, D.; Tavares, T. M.; Rocha, V. C.; Albaigés, J. Arch. Environ. Contam. Toxicol. 1990, 19, 263. Highly branched polyprenyl acetate, a yellow scale pheromone, has been isolated. Gieselmann, M. J.; Moreno, D. S.; Fargerlund, J.; Tashiro, H.; Roelofs, W. L. J. Chem. Ecol. 1979, 5, 27.
25. (a) Nagano, H; Kudo, K. Bull. Chem. Soc. Jpn. 1996, 69, 2071. (b) Nagano, H; Nagasawa, T; Sakuma, M. Bull. Chem. Soc. Jpn. 1997, 70, 1969.
26. (a) Nagano, H; Kudo, K. Bull. Chem. Soc. Jpn. 1996, 69, 2071. (b) Nagano, H; Nagasawa, T; Sakuma, M. Bull. Chem. Soc. Jpn. 1997, 70, 1969.
27. Phosphates 4a-6a, 4b-6b, 8, and 14, and disodium (E)-2-prenyl-geranyl phosphate derived from alcohol 25 (see ref. 12) formed liposomes in water. Y. Nakatani, personal communication.
28. (a) Shaw, J. E.; Kunerth, D. C.; Sherry, J. J. Tetrahedron Lett. 1973, 689. (b) Ahmad, I.; Gedye, R. N.; Nechvatal, A. J. Chem. Soc. (C) 1968, 185.
29. (a) Shaw, J. E.; Kunerth, D. C.; Sherry, J. J. Tetrahedron Lett. 1973, 689. (b) Ahmad, I.; Gedye, R. N.; Nechvatal, A. J. Chem. Soc. (C) 1968, 185.
30. r2. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813.
31. (a) Gedye, R. N.; Arora, P.; Khalil, A. H. Can. J. Chem. 1975 53, 1943. (b) Rice, L. E.; Boston, M. C.; Finklea, H. O.; Suder, B. J.; Frazier, J. O.; Hudlicky, T. J. Org. Chem. 1984, 49, 1845. (c) Bo, L.; Fallis, A. G. Tetrahedron Lett. 1986, 27, 5193. (d) Ballester, P.; García-Raso, A.; Mestres, R. Synthesis 1985, 802.
32. (a) Gedye, R. N.; Arora, P.; Khalil, A. H. Can. J. Chem. 1975 53, 1943. (b) Rice, L. E.; Boston, M. C.; Finklea, H. O.; Suder, B. J.; Frazier, J. O.; Hudlicky, T. J. Org. Chem. 1984, 49, 1845. (c) Bo, L.; Fallis, A. G. Tetrahedron Lett. 1986, 27, 5193. (d) Ballester, P.; García-Raso, A.; Mestres, R. Synthesis 1985, 802.
33. (a) Gedye, R. N.; Arora, P.; Khalil, A. H. Can. J. Chem. 1975 53, 1943. (b) Rice, L. E.; Boston, M. C.; Finklea, H. O.; Suder, B. J.; Frazier, J. O.; Hudlicky, T. J. Org. Chem. 1984, 49, 1845. (c) Bo, L.; Fallis, A. G. Tetrahedron Lett. 1986, 27, 5193. (d) Ballester, P.; García-Raso, A.; Mestres, R. Synthesis 1985, 802.
34. (a) Gedye, R. N.; Arora, P.; Khalil, A. H. Can. J. Chem. 1975 53, 1943. (b) Rice, L. E.; Boston, M. C.; Finklea, H. O.; Suder, B. J.; Frazier, J. O.; Hudlicky, T. J. Org. Chem. 1984, 49, 1845. (c) Bo, L.; Fallis, A. G. Tetrahedron Lett. 1986, 27, 5193. (d) Ballester, P.; García-Raso, A.; Mestres, R. Synthesis 1985, 802.
35. Yamamoto, Y.; Hori, A.; Hutchinson, C. R. J. Am. Chem. Soc. 1985, 107, 2471.
36. 4P: 301.1568.
37. (a) Lombarde, L. Tetrahedron Lett. 1982, 23, 4293. (b) Lombardo, L. Org. Synth. 1987, 65, 81. (c) Takai, K.; Hotta, Y.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1980, 53, 1698. (d) Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668.
38. (a) Lombarde, L. Tetrahedron Lett. 1982, 23, 4293. (b) Lombardo, L. Org. Synth. 1987, 65, 81. (c) Takai, K.; Hotta, Y.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1980, 53, 1698. (d) Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668.
39. (a) Lombarde, L. Tetrahedron Lett. 1982, 23, 4293. (b) Lombardo, L. Org. Synth. 1987, 65, 81. (c) Takai, K.; Hotta, Y.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1980, 53, 1698. (d) Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668.
40. (a) Lombarde, L. Tetrahedron Lett. 1982, 23, 4293. (b) Lombardo, L. Org. Synth. 1987, 65, 81. (c) Takai, K.; Hotta, Y.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1980, 53, 1698. (d) Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668.
41. Garner has reported the (E)-selective synthesis of trisubstituted olefins via a hydroxyl-directed Wittig reaction. The Wittig reaction of hydroxy ketone 40 under solvent-free conditions gave 41E selectively in 28% yield, but its purification was difficult. Garner, P.; Ramakanth, S. J. Org. Chem. 1987, 52, 2629.
42. Nozaki has reported the stereoselective synthesis of (2E)-5-bromo-3-methyl-2-penten-1-ol. However, in the synthesis the isolation of the starting material, 1-methyl-1-vinylcyclopropane by preparative GLC was required. Nakamura, H.; Yamamoto, H.; Nozaki, H. Tetrahedron Lett. 1973, 111. In the synthesis reported by Corey, the starting material, dimethyl E-methylglutaconate, has been separated from Z-isomer by fractional distillation. Corey, E. J.; Hamanaka, E. J. Am. Chem. Soc. 1967, 89, 2758.
43. Nozaki has reported the stereoselective synthesis of (2E)-5-bromo-3-methyl-2-penten-1-ol. However, in the synthesis the isolation of the starting material, 1-methyl-1-vinylcyclopropane by preparative GLC was required. Nakamura, H.; Yamamoto, H.; Nozaki, H. Tetrahedron Lett. 1973, 111. In the synthesis reported by Corey, the starting material, dimethyl E-methylglutaconate, has been separated from Z-isomer by fractional distillation. Corey, E. J.; Hamanaka, E. J. Am. Chem. Soc. 1967, 89, 2758.
44. Acid-catalyzed prenylation of prenyl acetate and geranyl acetate has been reported, (a) Julia, M.; Schmitz, C. Tetrahedron 1986, 42, 2485. (b) Julia, M.; Schmitz, C. Tetrahedron 1986, 42, 2491.
45. Acid-catalyzed prenylation of prenyl acetate and geranyl acetate has been reported, (a) Julia, M.; Schmitz, C. Tetrahedron 1986, 42, 2485. (b) Julia, M.; Schmitz, C. Tetrahedron 1986, 42, 2491.
46. (a) Yamamura, Y.; Umeyama, K.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1982, 23, 1933. (b) D. Babin, D.; Fourneron, J.-D.; Julia, M. Bull. Soc. Chim. Fr. 1980, II-588. (c) Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130.
47. (a) Yamamura, Y.; Umeyama, K.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1982, 23, 1933. (b) D. Babin, D.; Fourneron, J.-D.; Julia, M. Bull. Soc. Chim. Fr. 1980, II-588. (c) Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130.
48. (a) Yamamura, Y.; Umeyama, K.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1982, 23, 1933. (b) D. Babin, D.; Fourneron, J.-D.; Julia, M. Bull. Soc. Chim. Fr. 1980, II-588. (c) Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130.
49. Two possible biosynthetic routes of lavandulol 49 have been proposed: i) direct condensation of two prenyl diphosphate molecules, and ii) biosynthesis involving chrysanthemyl diphosphate (analogous to the biosynthesis of squalene). Epstein, W. W.; Klobus, M. A.; Edison, A. S. J. Org. Chem. 1991, 56, 4451.
50. Syntheses of lavandulol: (a) Fleming, I.; Lee, D. J. Chem. Soc., Perkin Trans. 1 1998, 2701. (b) Mino, T.; Fukui, S.; Yamashita, M. J. Org. Chem. 1997, 62, 734. (c) Imai, T.; Nishida, S. J. Chem. Soc., Chem. Commun. 1994, 277, and references cited therein.
51. Syntheses of lavandulol: (a) Fleming, I.; Lee, D. J. Chem. Soc., Perkin Trans. 1 1998, 2701. (b) Mino, T.; Fukui, S.; Yamashita, M. J. Org. Chem. 1997, 62, 734. (c) Imai, T.; Nishida, S. J. Chem. Soc., Chem. Commun. 1994, 277, and references cited therein.
52. Syntheses of lavandulol: (a) Fleming, I.; Lee, D. J. Chem. Soc., Perkin Trans. 1 1998, 2701. (b) Mino, T.; Fukui, S.; Yamashita, M. J. Org. Chem. 1997, 62, 734. (c) Imai, T.; Nishida, S. J. Chem. Soc., Chem. Commun. 1994, 277, and references cited therein.