Approach towards an EPC-synthesis of nodusmicin - IV. Construction of the highly hindered trisubstituted double bond of nodusmicin - IV. Construction of the highly hindered trisubstituted double bond of nodusmicin

Tetrahedron Letters

Volumn 38, Issue 37, 1997, Pages 6577-6580

  Auer, Edwin ^a   Gössinger, Edda ^a   Graupe, Michael ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT;

ARTICLE; DRUG SYNTHESIS;

EID: 0342437429     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01521-9     Document Type: Article

References (47)

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3. th Int. Symp. Chem. Synth. Antibiotics Rel. Microb. Prod. 1996.
4. Spectral data and experimental details are documented in the Ph.D. thesis of M.Graupe, Vienna 1997.
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14. The Evans' aldol reaction with α-ether aldehydes has been reported several times: Nicolaou, K.C.; Bertinato, P.; Piscopio, A.D.; Chakraborty; T.K.; Minova, N. J. Chem. Soc. Chem. Comm. 1993, 619-622; Evans, DA; Ratz, A.M.; Huff, B.E.; Sheppard, G.S. J. Am. Chem. Soc. 1995, 117, 3448-3467; Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakakura, A.; Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5330-5331; Kigoshi, H.; Ojika, M.; Suenaga, K.; Mutou, T.; Hirano, J.; Sakakura, A.; Ogawa, T.; Nisiwaki, M.; Yamada, K. Tetrahedron Lett. 1994, 35, 1247-1250; reversed stereochemistry was reported too: Evans, D.A.; Kaldor, S.W.; Jones, T.K.; Clardy, J.; Stout, T.J. J. Am. Chem. Soc. 1990, 112, esp. page 7009; Ewing, W.R.; Bhat, K.L.; Joullie, M.M. Tetrahedron 1986, 42, 5863-5868.
15. The Evans' aldol reaction with α-ether aldehydes has been reported several times: Nicolaou, K.C.; Bertinato, P.; Piscopio, A.D.; Chakraborty; T.K.; Minova, N. J. Chem. Soc. Chem. Comm. 1993, 619-622; Evans, DA; Ratz, A.M.; Huff, B.E.; Sheppard, G.S. J. Am. Chem. Soc. 1995, 117, 3448-3467; Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakakura, A.; Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5330-5331; Kigoshi, H.; Ojika, M.; Suenaga, K.; Mutou, T.; Hirano, J.; Sakakura, A.; Ogawa, T.; Nisiwaki, M.; Yamada, K. Tetrahedron Lett. 1994, 35, 1247-1250; reversed stereochemistry was reported too: Evans, D.A.; Kaldor, S.W.; Jones, T.K.; Clardy, J.; Stout, T.J. J. Am. Chem. Soc. 1990, 112, esp. page 7009; Ewing, W.R.; Bhat, K.L.; Joullie, M.M. Tetrahedron 1986, 42, 5863-5868.
16. The Evans' aldol reaction with α-ether aldehydes has been reported several times: Nicolaou, K.C.; Bertinato, P.; Piscopio, A.D.; Chakraborty; T.K.; Minova, N. J. Chem. Soc. Chem. Comm. 1993, 619-622; Evans, DA; Ratz, A.M.; Huff, B.E.; Sheppard, G.S. J. Am. Chem. Soc. 1995, 117, 3448-3467; Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakakura, A.; Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5330-5331; Kigoshi, H.; Ojika, M.; Suenaga, K.; Mutou, T.; Hirano, J.; Sakakura, A.; Ogawa, T.; Nisiwaki, M.; Yamada, K. Tetrahedron Lett. 1994, 35, 1247-1250; reversed stereochemistry was reported too: Evans, D.A.; Kaldor, S.W.; Jones, T.K.; Clardy, J.; Stout, T.J. J. Am. Chem. Soc. 1990, 112, esp. page 7009; Ewing, W.R.; Bhat, K.L.; Joullie, M.M. Tetrahedron 1986, 42, 5863-5868.
17. The Evans' aldol reaction with α-ether aldehydes has been reported several times: Nicolaou, K.C.; Bertinato, P.; Piscopio, A.D.; Chakraborty; T.K.; Minova, N. J. Chem. Soc. Chem. Comm. 1993, 619-622; Evans, DA; Ratz, A.M.; Huff, B.E.; Sheppard, G.S. J. Am. Chem. Soc. 1995, 117, 3448-3467; Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakakura, A.; Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5330-5331; Kigoshi, H.; Ojika, M.; Suenaga, K.; Mutou, T.; Hirano, J.; Sakakura, A.; Ogawa, T.; Nisiwaki, M.; Yamada, K. Tetrahedron Lett. 1994, 35, 1247-1250; reversed stereochemistry was reported too: Evans, D.A.; Kaldor, S.W.; Jones, T.K.; Clardy, J.; Stout, T.J. J. Am. Chem. Soc. 1990, 112, esp. page 7009; Ewing, W.R.; Bhat, K.L.; Joullie, M.M. Tetrahedron 1986, 42, 5863-5868.
18. The Evans' aldol reaction with α-ether aldehydes has been reported several times: Nicolaou, K.C.; Bertinato, P.; Piscopio, A.D.; Chakraborty; T.K.; Minova, N. J. Chem. Soc. Chem. Comm. 1993, 619-622; Evans, DA; Ratz, A.M.; Huff, B.E.; Sheppard, G.S. J. Am. Chem. Soc. 1995, 117, 3448-3467; Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakakura, A.; Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5330-5331; Kigoshi, H.; Ojika, M.; Suenaga, K.; Mutou, T.; Hirano, J.; Sakakura, A.; Ogawa, T.; Nisiwaki, M.; Yamada, K. Tetrahedron Lett. 1994, 35, 1247-1250; reversed stereochemistry was reported too: Evans, D.A.; Kaldor, S.W.; Jones, T.K.; Clardy, J.; Stout, T.J. J. Am. Chem. Soc. 1990, 112, esp. page 7009; Ewing, W.R.; Bhat, K.L.; Joullie, M.M. Tetrahedron 1986, 42, 5863-5868.
19. Penning, T.D.; Djuric, W.S.; Haack, R.A.; Kalish, V.J.; Miyashiro, J.M.; Rowell, B.W.; Yu, S.S. Synth. Commun. 1990, 20, 307-312.
20. Corey, E.J.; Pyne, S.G.; Su, W. Tetrahedron Lett. 1983, 4883-4886.
21. White, J.D.; Kawasaki, M. J. Org. Chem. 1992, 57, 5292-5300.
22. Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 4833-4836; Kocienski, P.J.; Lythgoe, B.; Ruston, S. J. Chem. Soc. Perk. I, 1978, 829-834; Keck, G.E.; Savin, K.A.; Weglarz, M.A. J. Org. Chem. 1995, 60, 3194-3204 and ref. cited therein. The improved one pot method by Julia, S.A.; Baudin, J.B.; Hareau, G.; Ruel, O. Bull. Chim. Soc.Fr. 1993, 130, 336-357; Julia, S.A.; Baudin, J.B.; Hareau, G.; Lorne, R.; Ruel, O. Bull. Chim. Soc.Fr. 1993, 130, 856-878; Smith, N.D.; Kocienski P.J. Street, S.D.A. Synthesis 1996, 652-666 has not been examined.
23. Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 4833-4836; Kocienski, P.J.; Lythgoe, B.; Ruston, S. J. Chem. Soc. Perk. I, 1978, 829-834; Keck, G.E.; Savin, K.A.; Weglarz, M.A. J. Org. Chem. 1995, 60, 3194-3204 and ref. cited therein. The improved one pot method by Julia, S.A.; Baudin, J.B.; Hareau, G.; Ruel, O. Bull. Chim. Soc.Fr. 1993, 130, 336-357; Julia, S.A.; Baudin, J.B.; Hareau, G.; Lorne, R.; Ruel, O. Bull. Chim. Soc.Fr. 1993, 130, 856-878; Smith, N.D.; Kocienski P.J. Street, S.D.A. Synthesis 1996, 652-666 has not been examined.
24. Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 4833-4836; Kocienski, P.J.; Lythgoe, B.; Ruston, S. J. Chem. Soc. Perk. I, 1978, 829-834; Keck, G.E.; Savin, K.A.; Weglarz, M.A. J. Org. Chem. 1995, 60, 3194-3204 and ref. cited therein. The improved one pot method by Julia, S.A.; Baudin, J.B.; Hareau, G.; Ruel, O. Bull. Chim. Soc.Fr. 1993, 130, 336-357; Julia, S.A.; Baudin, J.B.; Hareau, G.; Lorne, R.; Ruel, O. Bull. Chim. Soc.Fr. 1993, 130, 856-878; Smith, N.D.; Kocienski P.J. Street, S.D.A. Synthesis 1996, 652-666 has not been examined.
25. Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 4833-4836; Kocienski, P.J.; Lythgoe, B.; Ruston, S. J. Chem. Soc. Perk. I, 1978, 829-834; Keck, G.E.; Savin, K.A.; Weglarz, M.A. J. Org. Chem. 1995, 60, 3194-3204 and ref. cited therein. The improved one pot method by Julia, S.A.; Baudin, J.B.; Hareau, G.; Ruel, O. Bull. Chim. Soc.Fr. 1993, 130, 336-357; Julia, S.A.; Baudin, J.B.; Hareau, G.; Lorne, R.; Ruel, O. Bull. Chim. Soc.Fr. 1993, 130, 856-878; Smith, N.D.; Kocienski P.J. Street, S.D.A. Synthesis 1996, 652-666 has not been examined.
26. Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 4833-4836; Kocienski, P.J.; Lythgoe, B.; Ruston, S. J. Chem. Soc. Perk. I, 1978, 829-834; Keck, G.E.; Savin, K.A.; Weglarz, M.A. J. Org. Chem. 1995, 60, 3194-3204 and ref. cited therein. The improved one pot method by Julia, S.A.; Baudin, J.B.; Hareau, G.; Ruel, O. Bull. Chim. Soc.Fr. 1993, 130, 336-357; Julia, S.A.; Baudin, J.B.; Hareau, G.; Lorne, R.; Ruel, O. Bull. Chim. Soc.Fr. 1993, 130, 856-878; Smith, N.D.; Kocienski P.J. Street, S.D.A. Synthesis 1996, 652-666 has not been examined.
27. Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 4833-4836; Kocienski, P.J.; Lythgoe, B.; Ruston, S. J. Chem. Soc. Perk. I, 1978, 829-834; Keck, G.E.; Savin, K.A.; Weglarz, M.A. J. Org. Chem. 1995, 60, 3194-3204 and ref. cited therein. The improved one pot method by Julia, S.A.; Baudin, J.B.; Hareau, G.; Ruel, O. Bull. Chim. Soc.Fr. 1993, 130, 336-357; Julia, S.A.; Baudin, J.B.; Hareau, G.; Lorne, R.; Ruel, O. Bull. Chim. Soc.Fr. 1993, 130, 856-878; Smith, N.D.; Kocienski P.J. Street, S.D.A. Synthesis 1996, 652-666 has not been examined.
28. Martin, S.F.; Daniel, D.; Cherney, R.J.; Liras, S. J. Org. Chem. 1992, 57, 2523-2525.
29. Chamberlin, A.R.; Bloom, S.H. Org. Reactions 1990, 39, 1-83.
30. Dess, D.B.; Martin, J.C. J. Org. Chem. 1983, 48, 4155-4156.
31. 3): δ = 14.5 C-V1′ 130.9 C-3′, 138.1 C-2′.
32. Bowman, R.E. J. Chem. Soc. Perk. 1 1982, 1897-1903.
33. Gössinger, E.; Graupe, M.; Zimmermann, K. Monatsh. Chem. 1994, 125, 773-782.
34. McMurry, J.E. Chem. Rev. 1989, 1513-1524; McMurry, J.E.; Miller, D.D. J. Am. Chem. Soc. 1983, 105, 1660-1661; Fürstner, A., Jumban, D.N. Tetrahedron 1992, 48, 5991-6010.
35. McMurry, J.E. Chem. Rev. 1989, 1513-1524; McMurry, J.E.; Miller, D.D. J. Am. Chem. Soc. 1983, 105, 1660-1661; Fürstner, A., Jumban, D.N. Tetrahedron 1992, 48, 5991-6010.
36. McMurry, J.E. Chem. Rev. 1989, 1513-1524; McMurry, J.E.; Miller, D.D. J. Am. Chem. Soc. 1983, 105, 1660-1661; Fürstner, A., Jumban, D.N. Tetrahedron 1992, 48, 5991-6010.
37. Reductive cyclization of keto esters: Carlson, R.G., Blecke, R.G. J. Org. Chem. 1967, 32, 3538-3540; Gutsche, C.D.; Tao, I.Y.C.; Kozma, J. J. Org. Chem. 1967, 32, 1782-1790; Cook, I.F.; Knox, J.R. Tetrahedron 1976, 32, 363-367; 369-375; Nagaoka, H.; Shimano, M.; Yamada, Y. Tetrahedron Lett. 1989, 971-974.
38. Reductive cyclization of keto esters: Carlson, R.G., Blecke, R.G. J. Org. Chem. 1967, 32, 3538-3540; Gutsche, C.D.; Tao, I.Y.C.; Kozma, J. J. Org. Chem. 1967, 32, 1782-1790; Cook, I.F.; Knox, J.R. Tetrahedron 1976, 32, 363-367; 369-375; Nagaoka, H.; Shimano, M.; Yamada, Y. Tetrahedron Lett. 1989, 971-974.
39. Reductive cyclization of keto esters: Carlson, R.G., Blecke, R.G. J. Org. Chem. 1967, 32, 3538-3540; Gutsche, C.D.; Tao, I.Y.C.; Kozma, J. J. Org. Chem. 1967, 32, 1782-1790; Cook, I.F.; Knox, J.R. Tetrahedron 1976, 32, 363-367; 369-375; Nagaoka, H.; Shimano, M.; Yamada, Y. Tetrahedron Lett. 1989, 971-974.
40. Reductive cyclization of keto esters: Carlson, R.G., Blecke, R.G. J. Org. Chem. 1967, 32, 3538-3540; Gutsche, C.D.; Tao, I.Y.C.; Kozma, J. J. Org. Chem. 1967, 32, 1782-1790; Cook, I.F.; Knox, J.R. Tetrahedron 1976, 32, 363-367; 369-375; Nagaoka, H.; Shimano, M.; Yamada, Y. Tetrahedron Lett. 1989, 971-974.
41. 3 at -78°C, the keto group of 16 was reduced (40%) and only small amounts of the desired 16 (10%) were isolated. Compound 17 was not detected,
42. b) Under acyloin reaction conditions (Na/K, TMSCI, ether, rt) intramolecular coupling of 16 proceeded in good yields but led, due to overreduction, to the silylenolether.
43. c) With excess lithium naphthalide in THF at -78°C, 16 was converted via hydroxyketone 17 by deoxygenation to the corresponding ketone.
44. Screttas, C.G.; Micha-Screttas, M.M. J. Org. Chem. 1978, 43, 1064-1071.
45. Lohray, B.B. Synthesis 1992, 1035-1052; Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B. Chem. Rev. 1994, 94, 2483 pp 2515.
46. Lohray, B.B. Synthesis 1992, 1035-1052; Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B. Chem. Rev. 1994, 94, 2483 pp 2515.
47. 3): δ = 18.8 C-1′, 133.9 C-2′, 134.7 C-3′.