A practical total synthesis of both enantiomers of epoxyquinols A and B

Tetrahedron Letters

Volumn 43, Issue 50, 2002, Pages 9155-9158

  Shoji, Mitsuru ^a   Kishida, Satoshi ^a   Takeda, Mitsuhiro ^a   Kakeya, Hideaki ^b   Osada, Hiroyuki ^b   Hayashi, Yujiro ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b RIKEN   (Japan)

Author keywords

Diels Alder reaction; Epoxyquinols A and B; Lipase; Resolution

Indexed keywords

2 CYCLOHEXENONE; ALCOHOL DERIVATIVE; ANGIOGENESIS INHIBITOR; EPOXYQUINOL A; EPOXYQUINOL B; FURAN DERIVATIVE; LACTONE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; DIASTEREOISOMER; DIELS ALDER REACTION; DIMERIZATION; DRUG SYNTHESIS; ENANTIOMER; IODINATION; KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

BETULACEAE;

EID: 0037049185     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02271-2     Document Type: Article

References (29)

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13. For the Diels-Alder reaction of benzyl acrylate and furan, see: (a) Hayashi, Y.; Nakamura, M.; Nakao, S.; Inoue, T.; Shoji, M. Angew. Chem., Int. Ed., in press. For the Diels-Alder reaction of methyl acrylate and furan, see: (b) Kotsuki, H.; Asao, K.; Ohnishi, H. Bull. Chem. Soc. Jpn. 1984, 57, 3339; (c) Moore, J. A.; Partain, E. M., III. J. Org. Chem. 1983, 48, 1105; (d) Brion, F. Tetrahedron Lett. 1982, 23, 5299; (e) Fraile, J. M.; Garcia, J. I.; Massam, J.; Mayoral, J. A.; Pires, E. J. Mol. Catal. A: Chem. 1997, 123, 43; (f) Ager, D. J.; East, M. B. Heterocycles 1994, 37, 1789. For the Diels-Alder reaction under high pressure, see: (g) Kotsuki, H.; Nishizawa, H.; Ochi, M.; Matsuoka, K. Bull. Chem. Soc. Jpn. 1982, 55, 496; (h) Dauben, W. G.; Krabbenfoft, H. O. J. Am. Chem. Soc. 1976, 98, 1992. For the Diels-Alder reaction of acrylic acid and furan, see: (i) Suami, T.; Ogawa, S.; Nakamoto, K.; Kasahara, I. Carbohydr. Res. 1977, 58, 240 and references cited therein.
14. For the Diels-Alder reaction of benzyl acrylate and furan, see: (a) Hayashi, Y.; Nakamura, M.; Nakao, S.; Inoue, T.; Shoji, M. Angew. Chem., Int. Ed., in press. For the Diels-Alder reaction of methyl acrylate and furan, see: (b) Kotsuki, H.; Asao, K.; Ohnishi, H. Bull. Chem. Soc. Jpn. 1984, 57, 3339; (c) Moore, J. A.; Partain, E. M., III. J. Org. Chem. 1983, 48, 1105; (d) Brion, F. Tetrahedron Lett. 1982, 23, 5299; (e) Fraile, J. M.; Garcia, J. I.; Massam, J.; Mayoral, J. A.; Pires, E. J. Mol. Catal. A: Chem. 1997, 123, 43; (f) Ager, D. J.; East, M. B. Heterocycles 1994, 37, 1789. For the Diels-Alder reaction under high pressure, see: (g) Kotsuki, H.; Nishizawa, H.; Ochi, M.; Matsuoka, K. Bull. Chem. Soc. Jpn. 1982, 55, 496; (h) Dauben, W. G.; Krabbenfoft, H. O. J. Am. Chem. Soc. 1976, 98, 1992. For the Diels-Alder reaction of acrylic acid and furan, see: (i) Suami, T.; Ogawa, S.; Nakamoto, K.; Kasahara, I. Carbohydr. Res. 1977, 58, 240 and references cited therein.
15. For the Diels-Alder reaction of benzyl acrylate and furan, see: (a) Hayashi, Y.; Nakamura, M.; Nakao, S.; Inoue, T.; Shoji, M. Angew. Chem., Int. Ed., in press. For the Diels-Alder reaction of methyl acrylate and furan, see: (b) Kotsuki, H.; Asao, K.; Ohnishi, H. Bull. Chem. Soc. Jpn. 1984, 57, 3339; (c) Moore, J. A.; Partain, E. M., III. J. Org. Chem. 1983, 48, 1105; (d) Brion, F. Tetrahedron Lett. 1982, 23, 5299; (e) Fraile, J. M.; Garcia, J. I.; Massam, J.; Mayoral, J. A.; Pires, E. J. Mol. Catal. A: Chem. 1997, 123, 43; (f) Ager, D. J.; East, M. B. Heterocycles 1994, 37, 1789. For the Diels-Alder reaction under high pressure, see: (g) Kotsuki, H.; Nishizawa, H.; Ochi, M.; Matsuoka, K. Bull. Chem. Soc. Jpn. 1982, 55, 496; (h) Dauben, W. G.; Krabbenfoft, H. O. J. Am. Chem. Soc. 1976, 98, 1992. For the Diels-Alder reaction of acrylic acid and furan, see: (i) Suami, T.; Ogawa, S.; Nakamoto, K.; Kasahara, I. Carbohydr. Res. 1977, 58, 240 and references cited therein.
16. For the Diels-Alder reaction of benzyl acrylate and furan, see: (a) Hayashi, Y.; Nakamura, M.; Nakao, S.; Inoue, T.; Shoji, M. Angew. Chem., Int. Ed., in press. For the Diels-Alder reaction of methyl acrylate and furan, see: (b) Kotsuki, H.; Asao, K.; Ohnishi, H. Bull. Chem. Soc. Jpn. 1984, 57, 3339; (c) Moore, J. A.; Partain, E. M., III. J. Org. Chem. 1983, 48, 1105; (d) Brion, F. Tetrahedron Lett. 1982, 23, 5299; (e) Fraile, J. M.; Garcia, J. I.; Massam, J.; Mayoral, J. A.; Pires, E. J. Mol. Catal. A: Chem. 1997, 123, 43; (f) Ager, D. J.; East, M. B. Heterocycles 1994, 37, 1789. For the Diels-Alder reaction under high pressure, see: (g) Kotsuki, H.; Nishizawa, H.; Ochi, M.; Matsuoka, K. Bull. Chem. Soc. Jpn. 1982, 55, 496; (h) Dauben, W. G.; Krabbenfoft, H. O. J. Am. Chem. Soc. 1976, 98, 1992. For the Diels-Alder reaction of acrylic acid and furan, see: (i) Suami, T.; Ogawa, S.; Nakamoto, K.; Kasahara, I. Carbohydr. Res. 1977, 58, 240 and references cited therein.
17. For the Diels-Alder reaction of benzyl acrylate and furan, see: (a) Hayashi, Y.; Nakamura, M.; Nakao, S.; Inoue, T.; Shoji, M. Angew. Chem., Int. Ed., in press. For the Diels-Alder reaction of methyl acrylate and furan, see: (b) Kotsuki, H.; Asao, K.; Ohnishi, H. Bull. Chem. Soc. Jpn. 1984, 57, 3339; (c) Moore, J. A.; Partain, E. M., III. J. Org. Chem. 1983, 48, 1105; (d) Brion, F. Tetrahedron Lett. 1982, 23, 5299; (e) Fraile, J. M.; Garcia, J. I.; Massam, J.; Mayoral, J. A.; Pires, E. J. Mol. Catal. A: Chem. 1997, 123, 43; (f) Ager, D. J.; East, M. B. Heterocycles 1994, 37, 1789. For the Diels-Alder reaction under high pressure, see: (g) Kotsuki, H.; Nishizawa, H.; Ochi, M.; Matsuoka, K. Bull. Chem. Soc. Jpn. 1982, 55, 496; (h) Dauben, W. G.; Krabbenfoft, H. O. J. Am. Chem. Soc. 1976, 98, 1992. For the Diels-Alder reaction of acrylic acid and furan, see: (i) Suami, T.; Ogawa, S.; Nakamoto, K.; Kasahara, I. Carbohydr. Res. 1977, 58, 240 and references cited therein.
18. For the Diels-Alder reaction of benzyl acrylate and furan, see: (a) Hayashi, Y.; Nakamura, M.; Nakao, S.; Inoue, T.; Shoji, M. Angew. Chem., Int. Ed., in press. For the Diels-Alder reaction of methyl acrylate and furan, see: (b) Kotsuki, H.; Asao, K.; Ohnishi, H. Bull. Chem. Soc. Jpn. 1984, 57, 3339; (c) Moore, J. A.; Partain, E. M., III. J. Org. Chem. 1983, 48, 1105; (d) Brion, F. Tetrahedron Lett. 1982, 23, 5299; (e) Fraile, J. M.; Garcia, J. I.; Massam, J.; Mayoral, J. A.; Pires, E. J. Mol. Catal. A: Chem. 1997, 123, 43; (f) Ager, D. J.; East, M. B. Heterocycles 1994, 37, 1789. For the Diels-Alder reaction under high pressure, see: (g) Kotsuki, H.; Nishizawa, H.; Ochi, M.; Matsuoka, K. Bull. Chem. Soc. Jpn. 1982, 55, 496; (h) Dauben, W. G.; Krabbenfoft, H. O. J. Am. Chem. Soc. 1976, 98, 1992. For the Diels-Alder reaction of acrylic acid and furan, see: (i) Suami, T.; Ogawa, S.; Nakamoto, K.; Kasahara, I. Carbohydr. Res. 1977, 58, 240 and references cited therein.
19. For the Diels-Alder reaction of benzyl acrylate and furan, see: (a) Hayashi, Y.; Nakamura, M.; Nakao, S.; Inoue, T.; Shoji, M. Angew. Chem., Int. Ed., in press. For the Diels-Alder reaction of methyl acrylate and furan, see: (b) Kotsuki, H.; Asao, K.; Ohnishi, H. Bull. Chem. Soc. Jpn. 1984, 57, 3339; (c) Moore, J. A.; Partain, E. M., III. J. Org. Chem. 1983, 48, 1105; (d) Brion, F. Tetrahedron Lett. 1982, 23, 5299; (e) Fraile, J. M.; Garcia, J. I.; Massam, J.; Mayoral, J. A.; Pires, E. J. Mol. Catal. A: Chem. 1997, 123, 43; (f) Ager, D. J.; East, M. B. Heterocycles 1994, 37, 1789. For the Diels-Alder reaction under high pressure, see: (g) Kotsuki, H.; Nishizawa, H.; Ochi, M.; Matsuoka, K. Bull. Chem. Soc. Jpn. 1982, 55, 496; (h) Dauben, W. G.; Krabbenfoft, H. O. J. Am. Chem. Soc. 1976, 98, 1992. For the Diels-Alder reaction of acrylic acid and furan, see: (i) Suami, T.; Ogawa, S.; Nakamoto, K.; Kasahara, I. Carbohydr. Res. 1977, 58, 240 and references cited therein.
20. For the Diels-Alder reaction of benzyl acrylate and furan, see: (a) Hayashi, Y.; Nakamura, M.; Nakao, S.; Inoue, T.; Shoji, M. Angew. Chem., Int. Ed., in press. For the Diels-Alder reaction of methyl acrylate and furan, see: (b) Kotsuki, H.; Asao, K.; Ohnishi, H. Bull. Chem. Soc. Jpn. 1984, 57, 3339; (c) Moore, J. A.; Partain, E. M., III. J. Org. Chem. 1983, 48, 1105; (d) Brion, F. Tetrahedron Lett. 1982, 23, 5299; (e) Fraile, J. M.; Garcia, J. I.; Massam, J.; Mayoral, J. A.; Pires, E. J. Mol. Catal. A: Chem. 1997, 123, 43; (f) Ager, D. J.; East, M. B. Heterocycles 1994, 37, 1789. For the Diels-Alder reaction under high pressure, see: (g) Kotsuki, H.; Nishizawa, H.; Ochi, M.; Matsuoka, K. Bull. Chem. Soc. Jpn. 1982, 55, 496; (h) Dauben, W. G.; Krabbenfoft, H. O. J. Am. Chem. Soc. 1976, 98, 1992. For the Diels-Alder reaction of acrylic acid and furan, see: (i) Suami, T.; Ogawa, S.; Nakamoto, K.; Kasahara, I. Carbohydr. Res. 1977, 58, 240 and references cited therein.
21. . Holmes and co-workers elegantly synthesized cis-maneonene A using a similar sequence involving the Diels-Alder reaction of furan and fumaryl chloride, followed by hydrolysis and bromo-lactonization. See: Jennings-White C.L.D., Holmes A.B., Raithby P.R. J. Chem. Soc., Chem. Commun. 1979;542.
22. Mp 153.8-155.8°C ((±)-5: recrystallized from MeOH). Mp 153.8-156.2°C (unpurified (±)-5).
23. 3 solution was added until the color of iodine disappeared. After the organic solvent had been removed under reduced pressure, a white solid precipitated which was collected and dried to afford 62 g (0.23 mol) of iodolactone (±)-5 (42%).
24. To a solution of vinyl acetate (150 mL) of racemic cyclohexenol derivative (±)-6 (14.0 g, 82.5 mmol) was added P. stutzeri lipase (Meito TL) (1.40 g), and the reaction mixture was stirred vigorously for 40 h at room temperature. After filtration of the lipase, the volatile organic compounds were removed under reduced pressure and the remaining materials were purified by flash column chromatography (ethyl acetate:hexane=1:3-1:1) to afford (+)-6 (6.75 g, 49%, 99% ee) and (-)-7 (8.25 g, 48%, 96% ee).
25. HPLC conditions: Chiralcel OD-H column (Daicel Chemical Ind.), 2-propanol:hexane=1:20, 1.5 mL/min, retention times, 5.6 min (major), 6.0 min (minor).
26. HPLC conditions: Chiralcel OD-H column (Daicel Chemical Ind.), 2-propanol:hexane=1:20, 1.5 mL/min, retention times, 28.7 min (major), 11.1 min (minor).
27. Ohtani I., Kusumi T., Kashman Y., Kakisawa H. J. Am. Chem. Soc. 113:1991;4092.
28. Benhida R., Blanchard P., Fourrey J.-L. Tetrahedron Lett. 39:1998;6849.
29. Detailed biological study of both enantiomers of epoxyquinols A (1) and B (2) is underway, the results of which will be reported in due course.