Two-step conversion of 2-substituted furans into γ-oxo-α,β-unsaturated carboxylic acids. Formal synthesis of (+)-patulolide A and (-)-pyrenophorin

Tetrahedron Letters

Volumn 37, Issue 25, 1996, Pages 4385-4388

  Kobayashi, Yuichi ^a   Kishihara, Kiyonobu ^a   Watatani, Kengo ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; FURAN DERIVATIVE; HYPOCHLORITE SODIUM; NATURAL PRODUCT; PATULOLIDE A; PYRENOPHORIN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; INFRARED SPECTROSCOPY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0029884811     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00857-X     Document Type: Article

References (36)

1. (a) Boeckman, R. H. Jr.; Goldstein, S. W.: In The Total Synthesis of Natural Products; ApSimon, J. Ed.; John Wiley and Sons, Inc.: New York, 1988; Vol. 7, Chapter 1.
2. (b) Asaoka, M.; Takei, H. J. Synth. Org. Chem. Jpn. 1986, 44, 819-828.
3. Lipshutz, B. H. Chem. Rev. 1986, 86, 795-819.
4. (a) Hirsch, J. A.; Szur, A. J. J. Heterocycl. Chem. 1972, 9, 523-529.
5. (b) Hase, T. A.; Nylund, E.-L. Tetrahedron Lett. 1979, 2633-2636.
6. (c) Gunn, B. P. Tetrahedron Lett. 1985, 26, 2869-2872.
7. (a) Piancatelli, G.; Scettri, A.; D'Auria, M. Tetrahedron 1980, 36, 661-663.
8. (b) Petrini, M.; Ballini, R.; Rosini, G.; Marotta, E. Tetrahedron 1986, 42, 151-154.
9. Ngooi, T. K.; Scilimati, A.; Guo, Z.-w.; Sih, C. J. J. Org. Chem. 1989, 54, 911-914.
10. Oxidative conversions of 2,5-disubstituted furans to trans and/or cis 2-ene-1,4-diones have been reported: (a) Williams, P. D.; LeGoff, E. J. Org. Chem. 1981, 46, 4143-4147.
11. (b) Jurczak, J.; Pikul, S. Tetrahedron Lett. 1985, 26, 3039-3040.
12. (c) Pikul. S.; Raczko, J.; Ankner, K.; Jurczak, J. J. Am. Chem. Soc. 1987, 109, 3981-3987.
13. (a) Asaoka, M.; Yanagida, N.; Ishibashi, K.; Takei, H. Tetrahedron Lett. 1981, 22, 4269-4270.
14. (b) Asaoka, M.; Yanagida, N.; Takei, H. Tetrahedron Lett. 1980, 21, 4611-4614.
15. (c) Asaoka, M.; Yanagida, N.; Sugimura, N.; Takei, H. Bull. Chem. Soc. Jpn. 1980, 53, 1061-1064.
16. (d) Gunn, B. P.; Brooks, D. W. J. Org. Chem. 1985, 50, 4417-4418.
17. Watatani, K.; Kikori, Y.; Mizojiri, R.; Kobayashi, Y.: Unpublished result.
18. (a) Rodphaya, D.; Sekiguchi, J.; Yamada, Y. J. Antibiot. 1986, 39, 629-635.
19. (b) Makita, A.; Yamada, Y.; Okada, H. J. Antibiot. 1986, 39, 1257-1262.
20. (c) Mori, K.; Sakai, T. Liebigs Ann. Chem. 1988, 13-17.
21. (d) Solladié, G.; Gerber C. Synlett 1992, 449-450.
22. (a) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1977, 60, 2860-2865.
23. (b) Seuring, B.; Seebach, D. Liebigs Ann. Chem. 1978, 2044-2073.
24. (c) Labadie, J. W.; Tueting, D.; Stille, J. K. J. Org. Chem. 1983, 48, 4634-4642.
25. (d) Machinaga, N.: Kibayashi, C. Tetrahedron Lett. 1993, 34, 841-844.
26. (e) Matsushita, Y.; Furusawa, H.; Matsui, T.; Nakayama, M. Chem. Lett. 1994, 1083-1084.
27. (f) Nokami, J.; Taniguchi, T.; Gomyo, S.; Kakihara, T. Chem. Lett. 1994, 1103-1106.
28. (g) Bonete, P.; Nájera, C. J. Org. Chem. 1994, 59, 3202-3209.
29. (h) Barco, A.; Benetti, S.; Risi, C. D.; Pollini, G. P.; Zanirato, V. Tetrahedron 1995, 51, 7721-7726, and references cited therein.
30. Loupy, A.; Pardo, C. Synth. Commun. 1988, 18, 1275-1281.
31. Although (R)-propylene oxide is the best choice for preparation of 8, we selected 7 because it had been kindly provided by Daiso Co. Ltd.
32. Several hours at room temp, was necessary to isomerize the initially formed cis isomer to the trans one.
33. (a) Lindgren B. O.; Nilsson, T. Acta Chem. Scand. 1973, 27, 888-890.
34. (b) Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825-4830.
35. Synthesis of enantiopure 13: Noyori, R.; Ohkuma, T.: Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856-5858.
36. 2O (5 mL) and the resulting mixture was stirred for 1.5 h at room temperature. Most of the solvent was removed under reduced pressure and the residue was poured into a mixture of AcOEt and brine. The aqueous layer was acidified to pH ca 4 by addition of 1 N HCl. The organic layer was separated and the aqueous layer was extracted with AcOEt. Usual purification gave the title acid 11 (281 mg, 87% yield).