Progress toward the Synthesis of Garsubellin A and Related Phloroglucins: The Direct Diastereoselective Synthesis of the Bicyclo[3.3.1]nonane Core

Organic Letters

Volumn 4, Issue 11, 2002, Pages 1943-1946

  Spessard, Sarah J ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLINE ACETYLTRANSFERASE; CYCLOPEPTIDE; GARSUBELLIN A; LOBOCYCLAMIDE B; NEUROPROTECTIVE AGENT; TERPENE;

ALZHEIMER DISEASE; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ISOLATION AND PURIFICATION; MEDICINAL PLANT; METABOLISM; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALZHEIMER DISEASE; CHOLINE O-ACETYLTRANSFERASE; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NEUROPROTECTIVE AGENTS; PEPTIDES, CYCLIC; PLANTS, MEDICINAL; STEREOISOMERISM; TERPENES;

EID: 0037198742     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025968+     Document Type: Article

References (30)

1. Alzheimer's Association. Alzheimer's Vital Statistics. (http:// www.alz.org/research/current/stats.htm).
2. Fundamental Neuroscience; Zigmond, M. J., Bloom, F. E., Landis, S. C., Roberts, J. L., Squire, L. R., Eds.; Academic Press: San Diego, 1999; pp 216-219.
3. Auld, D. S.; Mennicken, F.; Day, J. C.; Quirion, R. J. Neurochemistry 2001, 77, 253.
4. Fukuyama, Y.; Kuwayama, A.; Minami, H. Chem. Pharm. Bull. 1997, 45, 947.
5. Nicolaou, K. C.; Pfefferkorn, J. A.; Kim, S.; Wei, H. X. J. Am. Chem. Soc. 1999, 121, 4724.
6. Usuda, H.; Kanai, M.; Shibasaki, M. Org. Lett. 2002, 4, 859.
7. For general reviews on remote diastereoselective induction in alkylations of enolate derivatives see: (a) Caine, D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, Chapter 1.1, pp 1-63. (b) Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 1, p. 1.
8. For general reviews on remote diastereoselective induction in alkylations of enolate derivatives see: (a) Caine, D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, Chapter 1.1, pp 1-63. (b) Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 1, p. 1.
9. For references dealing with the isolation of the compounds 5-8 shown in Figure 2, see: (a) Cuesta-Rubio, O.; Padron, A.; Castro, H. V.; Pizza, C.; Rastrelli, L. J. Nat. Prod. 2001, 64, 973. (b) Gurevich A. I.; Dobrynin, V. N.; Kolosov, M. N.; Popravko, S. A.; Ryabova, I. D.; Chernov, B. K.; Derbentseva, N. A.; Aizenman, B. E.; Garagulya, A. D. Antibiotiki (Moscow) 1971, 16, 510. (c) Gustafson, K. R.; Blunt, J. W.; Munro, M. H. G.; Fuller, R. W.; McKee, T. C.; Cardellina, J. H., II.; McMahon, J. B.; Cragg, G. M.; Boyd, M. R. Tetrahedron 1992, 48, 10093. (d) Winkelmann, K.; Heilmann, J.; Zerbe, O.; Rali, T.; Sticher, O. J. Nat. Prod. 2001, 64, 701.
10. For references dealing with the isolation of the compounds 5-8 shown in Figure 2, see: (a) Cuesta-Rubio, O.; Padron, A.; Castro, H. V.; Pizza, C.; Rastrelli, L. J. Nat. Prod. 2001, 64, 973. (b) Gurevich A. I.; Dobrynin, V. N.; Kolosov, M. N.; Popravko, S. A.; Ryabova, I. D.; Chernov, B. K.; Derbentseva, N. A.; Aizenman, B. E.; Garagulya, A. D. Antibiotiki (Moscow) 1971, 16, 510. (c) Gustafson, K. R.; Blunt, J. W.; Munro, M. H. G.; Fuller, R. W.; McKee, T. C.; Cardellina, J. H., II.; McMahon, J. B.; Cragg, G. M.; Boyd, M. R. Tetrahedron 1992, 48, 10093. (d) Winkelmann, K.; Heilmann, J.; Zerbe, O.; Rali, T.; Sticher, O. J. Nat. Prod. 2001, 64, 701.
11. For references dealing with the isolation of the compounds 5-8 shown in Figure 2, see: (a) Cuesta-Rubio, O.; Padron, A.; Castro, H. V.; Pizza, C.; Rastrelli, L. J. Nat. Prod. 2001, 64, 973. (b) Gurevich A. I.; Dobrynin, V. N.; Kolosov, M. N.; Popravko, S. A.; Ryabova, I. D.; Chernov, B. K.; Derbentseva, N. A.; Aizenman, B. E.; Garagulya, A. D. Antibiotiki (Moscow) 1971, 16, 510. (c) Gustafson, K. R.; Blunt, J. W.; Munro, M. H. G.; Fuller, R. W.; McKee, T. C.; Cardellina, J. H., II.; McMahon, J. B.; Cragg, G. M.; Boyd, M. R. Tetrahedron 1992, 48, 10093. (d) Winkelmann, K.; Heilmann, J.; Zerbe, O.; Rali, T.; Sticher, O. J. Nat. Prod. 2001, 64, 701.
12. For references dealing with the isolation of the compounds 5-8 shown in Figure 2, see: (a) Cuesta-Rubio, O.; Padron, A.; Castro, H. V.; Pizza, C.; Rastrelli, L. J. Nat. Prod. 2001, 64, 973. (b) Gurevich A. I.; Dobrynin, V. N.; Kolosov, M. N.; Popravko, S. A.; Ryabova, I. D.; Chernov, B. K.; Derbentseva, N. A.; Aizenman, B. E.; Garagulya, A. D. Antibiotiki (Moscow) 1971, 16, 510. (c) Gustafson, K. R.; Blunt, J. W.; Munro, M. H. G.; Fuller, R. W.; McKee, T. C.; Cardellina, J. H., II.;McMahon, J. B.; Cragg, G. M.; Boyd, M. R. Tetrahedron 1992, 48, 10093. (d) Winkelmann, K.; Heilmann, J.; Zerbe, O.; Rali, T.; Sticher, O. J. Nat. Prod. 2001, 64, 701.
13. Schönwälder, K.-H.; Kollat, P.; Stezowski, J. J.; Effenberger, F. Chem. Ber. 1984, 117, 3280.
14. To our knowledge, there are no related cyclizations of more densely functionalized substrates that utilize a bis-acyl bond construction.
15. Hara, R.; Furukawa, T.; Kashima, H.; Kusama, H.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1999, 121, 3072.
16. Stork, G.; Danheiser, R. L. J. Org. Chem. 1973, 38, 1775.
17. Johnson, W. S.; McCarry, B. E.; Markezich, R. L.; Boots, S. G. J. Am. Chem. Soc. 1980, 102, 352.
18. Laval, G.; Audran, G.; Galano, J.-M.; Monti, H. J. Org. Chem. 2000, 65, 3551.
19. Duhamel, P.; Hennequin, L.; Poirier, J. M.; Tavel, G.; Vottero, C. Tetrahedron 1986, 42, 4777.
20. Obtained as a 1:1 mixture of equilibrating enol isomers.
21. Crystallographic data have been deposited at the Cambridge Crystallographic Data Center under deposition number 173065.
22. Allyl ether 16 was obtained as a single enol ether isomer represented by the structure shown in Scheme 4 (by NOE analysis).
23. (a) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 7.2, pp 827-873.
24. (b) Blechert, S. Synthesis 1989, 71.
25. (c) Ziegler, F. E. Chem. Rev. 1988, 88, 1423.
26. (d) Ireland, R. E. Aldrichimica Acta 1988, 21, 59.
27. Obtained as a 1:1 mixture of separable enol ether isomers.
28. Isolated in addition to 30% yield of recovered enol ether 16.
29. See the preceding article in this issue: Chatterjee, A. K.; Sanders, D. P.; Grubbs, R. H. Org. Lett. 2002, 4, 1939.
30. For a recent review on the synthesis of [3.3.1] bicyclic compounds, see: Butkus, E. Synlett 2001, 12, 1827.