Tellurium in organic synthesis: A new approach to trisubstituted γ-butyrolactones with trans-trans relative stereochemistry. Total enantioselective synthesis of (-)-Blastmycinolactol, (+)-Blastmycinone, (-)-NFX-2, and (+)-Antimycinone

Tetrahedron Letters

Volumn 51, Issue 52, 2010, Pages 6843-6846

  Ferrarini, Renan S ^a   Dos Santos, Alcindo A ^a   Comasseto, João V ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

( ) Blastmycinolactol; ( ) NFX 2; Te Li exchange reaction; Butyrolactones

Indexed keywords

ANTIBIOTIC AGENT; ANTIMYCINONE; BLASTMYCINOLACTOL; BLASTMYCINONE; GAMMA BUTYROLACTONE DERIVATIVE; NFX 2; TELLURIUM; TELLURIUM DERIVATIVE; UNCLASSIFIED DRUG; VINYLIC HYDROXYTELLURIDE;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 78650680092     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.089     Document Type: Article

References (65)

1. (a) Yonehara, H.; Takeuchi, S.J. Antibiot., Ser. A 1958, 11, 254-263;
2. (b) Kinoshita, M.; Wada, M.; Umezawa, S. J. Antibiot. 1969, 22, 580-582;
3. (c) Liu, W. C.; van Tamelen, E. E.; Strong, F. M. J. Am. Chem. Soc. 1960, 82, 1652-1654.
4. Alali, F. Q.; Liu, X. X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540.
5. For enantioselective syntheses of compounds 1-4 see: (a) Chakraborty, T. K.; Chattopapadhyay, A. K.; Ghosh, S. Tetrahedron Lett. 2007, 48, 1139-1142;
6. (b) Yang, Y.-Q.; Wu, Y.-K. Chin. J. Chem. 2005, 23, 1519-1522;
7. (c) He, M.; Lei, A.; Zhang, X. Tetrahedron Lett. 2005, 46, 1823-1826;
8. (d) Krishna, P. R.; Ramana Reddy, V. V.; Sharma, G. V. M. Synthesis 2004, 13, 2107-2114;
9. (e) Peng, Z.-H.; Woerpel, K. A. Org. Lett. 2001, 3, 675-678;
10. (f) Nishiyama, T.; Nishioka, T.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Heterocycles 2001, 54, 69-72;
11. (g) Liu, R.-S. Pure Appl. Chem. 2001, 73, 265-269;
12. (h) Chen, M.-J.; Lo, C.-Y.; Chin, C.-C.; Liu, R.-S. J. Org. Chem. 2000, 65, 6362-6367;
13. (i) Esteve, C.; Ferreró, M.; Romea, P.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1999, 40, 5083-5086;
14. (j) Berkenbusch, T.; Bruckner, R. Tetrahedron 1998, 54, 11461-11470;
15. (k) Jacobi, P. A.; Herradura, P. Tetrahedron Lett. 1997, 38, 6621-6624;
16. (l) Sibi, M. P.; Lu, J.; Talbacka, C. L. J. Org Chem. 1996, 61, 7848-7855;
17. (m) Ishibashi, T.; Ochifuji, N.; Mori, M. Tetrahedron Lett. 1996, 37, 6165-6168;
18. (n) de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1995, 60, 4940-4942;
19. (o) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208;
20. (p) Nishide, K.; Aramata, A.; Kamanaka, T.; Inoue, T.; Node, M. Tetrahedron 1994, 50, 8337-8346;
21. (q) Nishide, K.; Aramata, A.; Kamanaka, T.; Node, M. Heterocycles 1993, 36, 2237-2240;
22. (r) Mukai, D.; Kataoka, O.; Hanaoka, M. J. Org. Chem. 1993, 58, 2946-2952;
23. (s) Mikami, K.; Terada, M.; Nakai, T. J. Chem. Soc., Chem. Commun. 1993, 343-345;
24. (t) Wasserman, H. H.; Gambale, R. J. Tetrahedron 1992, 48, 7059-7070;
25. (u) Inghardt, T.; Frejd, T. Tetrahedron 1991, 47, 6483-6492;
26. (v) Nishida, T.; Nihira, T.; Yamada, Y. Tetrahedron 1991, 47, 6623-6634;
27. (w) Mulzer, J.; Schulze, T.; Strecker, A.; Denzer, W. J. Org. Chem. 1988, 53, 4098-4103;
28. (x) Kobayashi, Y.; Uchiyama, H.; Kanbara, H.; Kusakabe, M. l.; Sato, F. Heterocycles 1987, 25, 549-561;
29. (y) Sayo, N.; Nakai, E.-i.; Nakai, T. Chem. Lett. 1985, 1723-1724;
30. (z) Uenishi, J.-i.; Tomozane, H.; Yamato, M. J. Chem. Soc., Chem. Commun. 1985, 717-719;
31. (aa) Uchiyama, H.; Kobayashi, Y.; Sato, F. Chem. Lett. 1985, 467-470;
32. (ab) Bernardi, A.; Beretta, M. G.; Colombo, L.; Gennari, C.; Poli, G.; Scolastico, C. J. Org. Chem. 1985, 50, 4442-4447;
33. (ac) Cardelach, J.; Font, J.; Ortuño, R. M. Tetrahedron Lett. 1985, 26, 2815-2816;
34. (ad) Wasserman, H. H.; Bambale, R. J. J. Am. Chem. Soc. 1985, 107, 1423-1424;
35. (ae) Fujisawa, T.; Kohama, H.; Tajima, K.; Sato, T. Tetrahedron Lett. 1984, 25, 5155-5156;
36. (af) Gennari, C.; Bernardi, A.; Cardani, S.; Scolastico, C. Tetrahedron 1984, 40, 4059-4065;
37. (ag) Abukaki, S.; Konishi, N.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1975, 48, 1254-1259;
38. (ah) Koyama, H.; Kogure, K.; Mori, K.; Matsui, M. Agr. Biol. Chem. 1973, 37, 915-920;
39. (ai) Kinoshita, M.; Abukaki, S.; Wada, M.; Umezawa, S. Bull. Chem. Soc. Jpn. 1973, 46, 1279-1287;
40. (aj) Kinoshita, M.; Abukaki, S.; Umezawa, S. J. Antibiot. 1972, 25, 373-376;
41. (ak) Kinoshita, M.; Wada, M.; Aburagi, S.; Umezawa, S. J. Antibiot. 1971, 24, 724-726.
42. Ugurchieva, T. M.; Veselovsky, V. V. Russ. Chem. Rev. 2009, 78, 337-373.
43. Bassora, B. K.; Costa, C. E.; Gariani, R. A.; Comasseto, J. V.; Dos Santos, A. A. Tetrahedron Lett. 2007, 48, 1485-1487.
44. (a) Zeni, G.; Formiga, H. B.; Comasseto, J. V. Tetrahedron Lett. 2000, 41, 1311-1313;
45. (b) Comasseto, J. V.; Barrientos-Astigarraga, R. E. Aldrichim. Acta 2000, 33, 66-78.
46. (a) Comasseto, J. V.; Gariani, R. A. Tetrahedron 2009, 65, 8447-8459;
47. (b) Dos Santos, A. A.; Da Costa, C. E.; Princival, J. L.; Comasseto, J. V. Tetrahedron: Asymmetry 2006, 17, 2252-2259.
48. For recent reviews see: (a) Petragnani, N.; Stefani, H. A. Tellurium in Organic Synthesis: Best Synthetic Methods, 2nd ed.; Academic Press: London, 2007;
49. (b) Comasseto, J. V.; Clososki, G. C.; Cunha, R. L. O. R. In Mingos, D. M. P., Crabtree, R. H., Eds.; Tellurium in: Comprehensive Organometallic Chemistry III; Elsevier: Amsterdam, 2007; Vol. 9, pp 587-648;
50. (c) Comasseto, J. V.; Dos Santos, A. A. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 939-947;
51. (d) Wendler, E. P.; Dos Santos, A. A. Synlett 2009, 7, 1034-1040.
52. For recent examples see: (a) Schneider, C. C.; Caldeira, H.; Gay, B. M.; Back, D. F.; Zeni, G. Org. Lett. 2010, 12, 936-939;
53. (b) Myrzayans, P. M.; Pouwer, R. H.; Williams, C. M. Org. Lett. 2008, 10, 3861-3863;
54. (c) Myrzayans, P. M.; Pouwer, R.H.; Williams, C. M.; Bernhardt, P. V. Tetrahedron 2009, 65, 8297-8305.
55. (a) Fleming, I.; Reddy, N. L.; Takaki, K.; Ware, A. C. J. Chem. Soc., Chem. Commun. 1987, 1472-1474;
56. (b) Harcken, C.; Rank, E.; Bruckner, R. Chem. Eur. J. 1998, 4, 2342-2352.
57. (a) Fleming, I.; Sanderson, P. E. J. Tetrahedron Lett. 1987, 28, 4229-4232;
58. (b) Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans. 1 1995, 317-337.
59. Ouchi, A.; Hyugano, T.; Liu, C. Org. Lett. 2009, 11, 4870-4876.
60. For (R)-5a and (S)-5a see: He, Y.-T.; Yang, H. N.; Yao, Z.-T. Tetrahedron 2002, 58, 8805-8810
61. (b) (S)-5b was derivatized to 9b and then the absolute configuration was determined by comparing the optical rotation value of the 9b, with that described in Ref. 3j for the same compound..
62. 1 H NMR data with those described in the literature3j for the same molecules.
63. 3).
64. 3).
65. 3j56-57 °C; CAS [137171-29-0].