Lasonolide A: Synthesis of A and B rings via a cycloetherification strategy

Synlett

Volumn , Issue 9 SPEC. ISS., 2003, Pages 1334-1338

  Hart, David J ^a   Patterson, Suzanne ^a   Unch, James P ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Cycloetherification; Lasonolide A; Macrolide; Phenylselenenyl chloride; Tetrahydropyran

Indexed keywords

ALLYL ALCOHOL; ANTINEOPLASTIC AGENT; LASONOLIDE A; NATURAL PRODUCT; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; CYCLOETHERIFICATION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0037765542     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40323     Document Type: Article

References (40)

1. Horton, P. A.; Koehn, F. E.; Longley, R. E.; McConnell, O. J. J. Am. Chem. Soc. 1994, 116, 6015.
2. (a) Lee, E.; Song, H. Y.; Kang, J. W.; Kim, D.-S.; Jung, C.-K.; Joo, J. M. J. Am. Chem. Soc. 2002, 124, 384.
3. (b) Lee, E.; Song, H. Y.; Joo, J. M.; Kang, J. W.; Kim, D. S.; Jung, C. K.; Hong, C. Y.; Jeong, S. W.; Jeon, K. Bioorg. Med. Chem. Lett. 2002, 12, 3519.
4. For biological activity see: Longley, R. E.; Harmody, D. J. Antibiot. 1991, 44, 93.
5. For synthetic studies see ref. 2 and: (a) Gurjar, M. K.; Kumar, P.; Rao, B. V. Tetrahedron Lett. 1996, 37, 8617. (b) Gurjar, M. K.; Chakrabarti, A.; Rao, B. V.; Kumar, P. Tetrahedron Lett. 1997, 38, 6885. (c) Nowakowski, M.; Hoffmann, H. M. R. Tetrahedron Lett. 1997, 38, 1001. (d) Beck, H.; Hoffmann, H. M. R. Eur. J. Org. Chem. 1999, 2991.
6. For synthetic studies see ref. 2 and: (a) Gurjar, M. K.; Kumar, P.; Rao, B. V. Tetrahedron Lett. 1996, 37, 8617. (b) Gurjar, M. K.; Chakrabarti, A.; Rao, B. V.; Kumar, P. Tetrahedron Lett. 1997, 38, 6885. (c) Nowakowski, M.; Hoffmann, H. M. R. Tetrahedron Lett. 1997, 38, 1001. (d) Beck, H.; Hoffmann, H. M. R. Eur. J. Org. Chem. 1999, 2991.
7. For synthetic studies see ref. 2 and: (a) Gurjar, M. K.; Kumar, P.; Rao, B. V. Tetrahedron Lett. 1996, 37, 8617. (b) Gurjar, M. K.; Chakrabarti, A.; Rao, B. V.; Kumar, P. Tetrahedron Lett. 1997, 38, 6885. (c) Nowakowski, M.; Hoffmann, H. M. R. Tetrahedron Lett. 1997, 38, 1001. (d) Beck, H.; Hoffmann, H. M. R. Eur. J. Org. Chem. 1999, 2991.
8. For synthetic studies see ref. 2 and: (a) Gurjar, M. K.; Kumar, P.; Rao, B. V. Tetrahedron Lett. 1996, 37, 8617. (b) Gurjar, M. K.; Chakrabarti, A.; Rao, B. V.; Kumar, P. Tetrahedron Lett. 1997, 38, 6885. (c) Nowakowski, M.; Hoffmann, H. M. R. Tetrahedron Lett. 1997, 38, 1001. (d) Beck, H.; Hoffmann, H. M. R. Eur. J. Org. Chem. 1999, 2991.
9. Hart, D. J.; Leroy, V.; Merriman, G. H.; Young, D. G. J. J. Org. Chem. 1992, 57, 5670.
10. Hart, D. J.; Patterson, S.; Zakarian, A. Heterocycles 2000, 52, 1025; and references cited therein.
11. Andersson, F.; Samuelsson, B. Carbohydr. Res. 1984, 129, C1.
12. Albrecht, H. P.; Moffatt, J. G. Tetrahedron Lett. 1970, 11, 1063.
13. Ali, Y.; Vyas, D. M.; Nabinger, R. C.; Szarek, W. A. Carbohydr. Res. 1982, 104, 183.
14. Ceccherelli, P.; Curini, M.; Marcotullio, M. C.; Epifano, F.; Rosati, O. Synth. Commun. 1998, 28, 3057.
15. Iversen, T.; Bundle, D. R. J. Chem. Soc., Chem. Commun. 1981, 1240.
16. Garegg, P. J.; Samuelsson, B. Synthesis 1979, 469.
17. Ghosh, T.; Hart, H. J. Org. Chem. 1989, 54, 5073.
18. Kuivila, H. G.; Sommer, R. J. Am. Chem. Soc. 1967, 89, 5616.
19. For seminal studies on PhSeCl-initiated cycloetherifications, see: Nicolaou, K. C.; Magolda, R. L.; Sipio, W. J.; Barnette, W. E.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 3784.
20. Clive, D. L. J.; Chittattu, G.; Wong, C. K. J. Chem. Soc., Chem. Commun. 1978, 41.
21. Kusakabe, M.; Kitano, Y.; Kobayashi, Y.; Sato, F. J. Org. Chem. 1989, 54, 2085.
22. Hanessian, S.; Lavallee, P. Can. J. Chem. 1975, 53, 2975.
23. 13C NMR spectra of 2 and 3.
24. (a) Lewis, N.; McKen, P. W.; Taylor, R. J. K. Synlett 1991, 898.
25. (b) Bellassoued, M.; Salemkour, M. Tetrahedron 1996, 52, 4607.
26. Nagao, Y.; Kumagai, T.; Tamai, S.; Abe, T.; Kuramoto, Y.; Taga, T.; Aoyagi, S.; Nagase, Y.; Ochiai, M.; Inoue, Y.; Fujita, E. J. Am. Chem. Soc. 1986, 108, 4673.
27. Garigipati, R. S.; Tschaen, D. M.; Weinreb, S. M. J. Am. Chem. Soc. 1985, 107, 7790.
28. Corey, E. J.; Link, J. O. Tetrahedron Lett. 1990, 31, 601.
29. (a) Still, W. C. J. Am. Chem. Soc. 1978, 100, 1481.
30. (b) Kaufman, T. S. Synlett 1997, 1377.
31. (a) Hara, O.; Ito, M.; Hamada, Y. Tetrahedron Lett. 1998, 39, 5537.
32. (b) Wipf, P.; Methot, J. L. Org. Lett. 2001, 3, 1261.
33. Nakata, T.; Tani, Y.; Hatozaki, M.; Oishi, T. Chem. Pharm. Bull. 1984, 32, 1411.
34. We thank Dr. Judith C. Gallucci for determining the structure of 40 at the OSU Chemistry Department Crystallographic Facility.
35. 6 p-methoxystyryl group with phenyl, 2-furyl, styryl). In all cases the structure corresponding to 35 was the major product in 60-70% yield. In one case (styryl) a minor diastereomer (5%) was detected in which all substituents were equatorially disposed on the tetrahydropyran ring with the exception of the benzyloxymethyl group (axially disposed).
36. Dalton, D. R.; Dutta, V. P.; Jones, D. G. J. Am. Chem. Soc. 1968, 90, 5498.
37. Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull Chem. Soc. Jpn. 1989, 62, 143.
38. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
39. Ha, D. C.; Hart, D. J. J. Antibiotics 1987, 40, 309.
40. Some of the reagents used in Schemes 1 and 2 are toxic (for example PhSeCl). Appropriate care should be used in the handling and disposal of these materials.