Synthesis of (±)-(4aα,6α,7α,7aα)-hexahydro-6-hydroxy-7- methylcyclopenta[c]pyran-3(1H)-one, a structure common to abelialactone, Aglykon A1, and isoboonein

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 3, 1996, Pages 525-529

  Ohba, Masashi ^a   Haneishi, Tsuyoshi ^a   Fujii, Tozo ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

1,3 dioxin vinylogous ester; abelialactone; Aglykon A1; carboxyolefination; cyclopentano monoterpene lactone; isoboonein

Indexed keywords

ABELIALACTONE; AGLYKON A1; ISOBOONEIN; LACTONE DERIVATIVE; PYRAN DERIVATIVE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0029975095     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.525     Document Type: Article

References (27)

1. For reviews on cyclopentano-monoterpene lactones, see a) Cavill G. W. K., Pure Appl. Chem., 10, 169-183 (1960) b) Sakan T., Murai F., Isoe S., Hyeon S. B., Hayashi Y., Nippon Kagaku Zasshi, 90, 507-528 (1969) c) El-Naggar L. J., Beal J. L., J. Nat. Prod., 43, 649-707 (1980) d) Boros C. A., Stermitz F. R., ibid., 54, 1173-1246 (1991)
2. For reviews on cyclopentano-monoterpene lactones, see a) Cavill G. W. K., Pure Appl. Chem., 10, 169-183 (1960) b) Sakan T., Murai F., Isoe S., Hyeon S. B., Hayashi Y., Nippon Kagaku Zasshi, 90, 507-528 (1969) c) El-Naggar L. J., Beal J. L., J. Nat. Prod., 43, 649-707 (1980) d) Boros C. A., Stermitz F. R., ibid., 54, 1173-1246 (1991)
3. For reviews on cyclopentano-monoterpene lactones, see a) Cavill G. W. K., Pure Appl. Chem., 10, 169-183 (1960) b) Sakan T., Murai F., Isoe S., Hyeon S. B., Hayashi Y., Nippon Kagaku Zasshi, 90, 507-528 (1969) c) El-Naggar L. J., Beal J. L., J. Nat. Prod., 43, 649-707 (1980) d) Boros C. A., Stermitz F. R., ibid., 54, 1173-1246 (1991)
4. For reviews on cyclopentano-monoterpene lactones, see a) Cavill G. W. K., Pure Appl. Chem., 10, 169-183 (1960) b) Sakan T., Murai F., Isoe S., Hyeon S. B., Hayashi Y., Nippon Kagaku Zasshi, 90, 507-528 (1969) c) El-Naggar L. J., Beal J. L., J. Nat. Prod., 43, 649-707 (1980) d) Boros C. A., Stermitz F. R., ibid., 54, 1173-1246 (1991)
5. Murai F., Tagawa M , Abstracts of Papers, 29th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Tsu, October 1985, pp. 286-288.
6. Murai F., Tagawa M., Matsuda S., Kikuchi T., Uesato S., Inouye H., Phytochemistry, 24, 2329-2335 (1985).
7. Schneider K., Jurenitsch J., Jentzsch K., Sci Pharm., 54, 339-345 (1986).
8. Bianco A., De Luca A., Mazzei R. A , Nicoletti M., Passacantilli P., De Lima R. A., Phytochemistry, 35, 1485-1487 (1994).
9. Ohba M., Haneishi T., Fujii T., Heterocycles, 38, 2253-2260 (1994).
10. Ohba M., Haneishi T., Fujii T., Chem. Pharm. Bull., 43, 26-31 (1995).
11. For the syntheses of the macrocyclic diterpenes utilizing the 1,3-dioxin vinylogous ester 4, see a) Smith A. B., III, "Strategies and Tactics in Organic Synthesis," ed. by Lindberg T., Academic Press, Orland. 1984, Chapter 9 b) Smith A. B., III, Dorsey B. D., Visnick M., Maeda T., Malamas M. S., J. Am. Chem. Soc., 108, 3110-3112 (1986) c) Smith A. B., III, Lupo A. T., Jr., Ohba M., Chen K., ibid., 111, 6648-6656 (1989).
12. For the syntheses of the macrocyclic diterpenes utilizing the 1,3-dioxin vinylogous ester 4, see a) Smith A. B., III, "Strategies and Tactics in Organic Synthesis," ed. by Lindberg T., Academic Press, Orland. 1984, Chapter 9 b) Smith A. B., III, Dorsey B. D., Visnick M., Maeda T., Malamas M. S., J. Am. Chem. Soc., 108, 3110-3112 (1986) c) Smith A. B., III, Lupo A. T., Jr., Ohba M., Chen K., ibid., 111, 6648-6656 (1989).
13. For the syntheses of the macrocyclic diterpenes utilizing the 1,3-dioxin vinylogous ester 4, see a) Smith A. B., III, "Strategies and Tactics in Organic Synthesis," ed. by Lindberg T., Academic Press, Orland. 1984, Chapter 9 b) Smith A. B., III, Dorsey B. D., Visnick M., Maeda T., Malamas M. S., J. Am. Chem. Soc., 108, 3110-3112 (1986) c) Smith A. B., III, Lupo A. T., Jr., Ohba M., Chen K., ibid., 111, 6648-6656 (1989).
14. Smith A. B., III, Dorsey B. D., Ohba M., Lupo A. T., Jr., Malamas M. S., J. Org Chem., 53, 4314-4325 (1988).
15. Holton R. A., Somoza C., Kim H.-B., Liang F., Biediger R. J., Boatman P. D., Shindo M., Smith C. C., Kim S., Nadizadeh H., Suzuki Y., Tao C., Vu P., Tang S., Zhang P., Murthi K. K., Gentile L. N., Liu J H., J. Am. Chem. Soc., 116, 1597-1598 (1994).
16. Loza E., Lola D., Freimanis J., Turovskis I., Rozite S., Bokaldere R., Sahartova O., Tetrahedron, 44, 1207-1219 (1988).
17. Kalinowski H.-O., Berger S., Braun S., "Carbon-13 NMR Spectroscopy," John Wiley and Sons, Inc., New York, 1988, Chapter 3.
18. a) Arhart R. J . Martin J. C., J. Am. Chem. Soc., 94, 5003-5010 (1972)
19. b) Martin J. C., Arhart R. J., Franz J A., Perozzi E. F., Kaplan L. J., "Organic Syntheses," Coll. Vol. 6, ed. by Noland W. E., John Wiley and Sons. Inc., New York, 1988, pp. 163-166.
20. a) Sisido K., Inomata K., Kageyema T., Utimoto K., J. Org. Chem., 33, 3149-3155 (1968)
21. b) Bellesia F., Pagnoni U. M., Trave R., Andreetti G. D., Bocelli G., Sgarabotto P., J. Chem Soc., Perkin Trans. 2, 1979, 1341-1346.
22. Kocsis Á., Szabó L. F., Podányi B., J. Nat. Prod., 56, 1486-1499 (1993).
23. 3 was newly measured by Professor F. Murai for comparison with that of (±)-1.
24. 4)
25. 5)
26. Still W. C., Kahn M., Mitra A., J. Org. Chem., 43, 2923-2925 (1978).
27. Davis F. A., Towson J C., Weismiller M. C., LaI S., Carroll P. J., J. Am. Chem. Soc., 110, 8477-8482 (1988).