Synthesis of Side Chain Truncated 3″-Aldehyde, 3″-Carboxylic Acid, and 1″-Aldehyde from Nodulisporic Acid A

Organic Letters

Volumn 4, Issue 8, 2002, Pages 1291-1294

  Chakravarty, Prasun K ^a   Tyagarajan, Sriram ^a   Shih, Thomas L ^a   Salva, Steve ^a   Snedden, Christine ^a   Wyvratt, Matthew J ^a   Fisher, Michael H ^a   Meinke, Peter T ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBOXYLIC ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; INDOLE DERIVATIVE; INSECTICIDE; NODULISPORIC ACID A;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALDEHYDES; CARBOXYLIC ACIDS; INDICATORS AND REAGENTS; INDOLES; INSECTICIDES; OXIDATION-REDUCTION;

EID: 0037129410     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025766d     Document Type: Article

References (48)

1. Ondeyka, J. G.; Helms, G. L.; Hensens, O. D.; Goetz, M. A.; Zink, D. L.; Tsipouras, A.; Shoop, W. L.; Slayton, L.; Dombrowski, A. W.; Polishook, J. D.; Ostlind, D. A.; Tsou, N. N.; Ball, R. G.; Singh, S. B. J. Am. Chem. Soc. 1997, 119, 8809.
2. Hensens, O. D.; Ondeyka, J. G.; Dombrowski, A. W.; Ostlind, D. A.; Zink, D. L. Tetrahedron Lett. 1999, 40, 5455.
3. Ostlind, D. A.; Felcetto, T.; Misura, A.; Ondeyka, J.; Smith, S.; Goetz, M.; Shoop, W.; Mickle, W. Med. Vet. Entomol. 1997, 11, 407.
4. Shoop, W. L.; Gregory, L. M.; Zakson-Aiken, M.; Michael, B. F.; Haines, H. W.; Ondeyka, J. G.; Meinke, P. T.; Schmatz, D. M. J. Parasitol. 2001, 87, 419.
5. Smith, M. M.; Warren, V. A.; Thomas, B. S.; Brochu, R. M.; Ertel, E. A.; Rohrer, S.; Schaeffer, J.; Schmatz, D.; Petuch, B. R.; Tang, Y. S.; Meinke, P. T.; Kaczorowski, G. J.; Cohen, C. J. Biochemistry 2000, 39, 5543.
6. (a) Meinke, P. T.; Ayer, M. B.; Colletti, S. L.; Li, C.; Lim, J.; Ok, D.; Salva, S.; Shih, T. L.; Wyvratt, M. J.; Shoop, W. L.; Gregory, L. M.; Schmatz, D. M.; Fisher, M. H. Bioorg. Med. Chem. Lett. 2000, 10, 2371.
7. (b) While chemical modifications at the permissive region of NsA A could be tolerated, the nonpermissive region of the molecule appeared to be essential for the maintenance of the biological activity.
8. Shoop, W. L.; Gregory, L. M.; Zakson-Aiken, M.; Michael, B. F.; Pivnichny, J.; Meinke, P. T.; Fisher, M. H.; Wyvratt, M. J.; Schmatz, D. M. J. Parasitol. 2001, 87, 1150.
9. (a) Tyagarajan, S.; Chakravarty, P. K.; Wyvratt, M. J.; Fisher, M. H.; Meinke, P. T.; Schmatz, D. M.; Shoop, W. L.; Warmke, L. M.; Zakson-Aiken, M. Abstracts of Papers, The 221st National Meeting of the American Chemical Society, San Diego, CA, April 1-5, 2001; American Chemical Society: Washington, DC: Abstract 245.
10. (b) Ayer, M. B.; Chakravarty, P. K.; Meinke, P. T.; Shih, T. L.; Wyvratt, M. J.; Fisher, M. H.; Warmke, L. M.; Zakson-Aiken, M.; Shoop, W. L.; Schmatz, D. M. Abstracts of Papers, The 222nd National Meeting of the American Chemical Society, Chicago, IL, August 26-30, 2001; American Chemical Society: Washington, DC; Abstract 245.
11. (c) Berger, R.; Shoop, W. L.; Pivnichny, J. V.; Warmke, L. M.; Zackson-Aiken, M.; Owens, K. A.; Demontgney, P.; Schmatz, D. M.; Wyvratt, M. J.; Fisher, M. H.; Meinke, P. T.; Colletti, S. L. Org. Lett. 2001, 3, 3715.
12. 12,13 under a variety of conditions was also unsuccessful due to the rapid and complete degradation of 1.
13. Iwata, C.; Takemoto, Y.; Nakamura, A.; Imanishi, T. Tetrahedron Lett. 1985, 26, 3227.
14. Wolfe, S.; Hasan, S. K.; Campbell, J. R. J. Chem. Soc., Chem. Comm. 1970, 1420.
15. Chakraborti, A. K.; Ghatak, U. R. J. Chem. Soc., Perkin Trans. 1 1985, 2605.
16. Martin, V. S.; Palazon, J. M.; Rodriguez, C. M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L., Ed.; John Wiley & Sons: New York, 1995; Vol. 6, pp 4415-4422,
17. Pappo, R.; Allen, D. S., Jr.; Lemieux, R. U.; Johnson, W. S. J. Org. Chem. 1956, 21, 478.
18. Viski, P.; Sezeverenyi, Z.; Simandi, L. I. J. Org. Chem. 1986, 51, 3213.
19. 8 methyl group.
20. 4 under standard conditions produced a mixture of two aldehydes 3 and 5, separable by chromatography, in 24 and 2% yields, respectively, along with a mixture of unidentified over-oxidation products.
21. Herrman, W. A.; Eder, S.; Scherer, W. Angew. Chem., Int. Ed. Engl. 1992, 31, 1345.
22. 4 to the 3″,4″-double bond was anticipated in the case of electron-rich amide 7.
23. 19 double bond) along with the desired products.
24. 4), and concentrated. The crude diols 10 (190 mg) (containing ∼10% 3) obtained were used in the next step without purification. The diastereoisomers of 10 could be separated by silica gel chromatography using EtOAc-hexane (2:1).
25. Corey, E. J.; Xiang, Y. B. Tetrahedron Lett. 1988, 29, 995.
26. 2 = 13.4 Hz, 1H), 2.01 (br s, 1H), 1.40-1.90 (m, 8H), 1.51 (s, 3H), 1.46 (br s, 3H), 1.38 (s, 3H), 1.36 (s, 3H), 1.17 (s, 6H), 1.12 (s, 3H), 0.98 (s, 3H). MS m/e: 624.4 (M + 1).
27. Cleavage of diols 10 with sodium periodate was also probed under a variety of conditions, but in all instances, the yields were inferior.
28. 1H NMR and mass spectrometry.
29. For a review of oxidative cleavages of C=C bonds, see: Hudlicky, M. Oxidations in Organic Chemistry; American Chemical Society; Washington, DC, 1990; pp 77, 96.
30. (a) Sam, D. J.; Simmons, H. E. J. Am. Chem. Soc. 1972, 94, 4024.
31. (b) Lee, D. G.; Chang, V. S. J. Org. Chem. 1978, 43, 1532.
32. (a) Hazra, B. G.; Kumar, T. P.; Joshi, P. L. Liebigs Ann./Recl. 1997, 1029.
33. (b) Bhushan, V.; Rathore, R.; Chandrasekaran, S. Synthesis 1984, 5, 431.
34. (c) Reischl, W.; Zbiral, E. Tetrahedron 1979, 35, 1109.
35. Reaction of 1 with CTAP gave 3 in 40% yield along with unreacted 1 (∼50%), which was readily recycled. While this reaction failed to go to completion, the nonpolar 3 was readily separable from unreacted acid 1. Low levels of the corresponding 1″-aldehyde 5 (<5 %) was also obtained from this reaction, presumably via the intermediacy of the 1″,2″3″,4″-tetra-ol of 1.
36. (a) Quici, S.; Regen, S. L. J. Org. Chem. 1979, 44, 3436.
37. (b) Menger, F. M.; Lee, D. G. J. Org. Chem. 1979, 44, 2446.
38. (c) Ferreira, J. T.; Cruz, W. O.; Vieira, P. C.; Yonashiro, M. J. Org. Chem. 1987, 52, 3698.
39. (d) Lee, D. J.; Chen, T.; Wang, Z. J. Org. Chem. 1993, 58, 2918.
40. 2 as an eluant followed by EtOAc. The solvents were removed under reduced pressure at ambient temperature to yield pure 3 (2.6 g, 94%).
41. (a) Hillis, L. R.; Ronald, R. C. J. Org. Chem. 1985, 50, 470.
42. (b) Gorgen, G.; Boland, W.; Preiss, U.; Simon, H. Helv. Chem. Acta. 1989, 72, 917.
43. 2 = 13.4 Hz, 1H), 2.01 (br s, 1H), 1.40-1.90 (m, 8H), 1.51 (s, 3H), 1.46 (br s, 3H), 1.38 (s, 3H), 1.36 (s, 3H), 1.16 (s, 3H), 1.15 (s, 3H), 1.09 (s, 3H), 0.96 (s, 3H). MS mle: 640.6 (M + 1).
44. 3CN (3 mL) were then added. After 3 h, the solvent was removed under reduced pressure and the residue dried in vacuo for 1 h to yield to pure 7,24-bis-O-trimethylsilyl 3″-aldehyde 11a (0.87 g, 100%), which required no purification.
45. Hart, T. W.; Metcalf, D. A.; Scheinmann, F. J. Chem. Soc. Chem. Commun. 1979, 156.
46. 2SO4) The solution was filtered and concentrated under reduced pressure. Pure bis-OTES-3″-acid 12b (0.73 g) was obtained following flash chromatography on silica gel using gradient elution with 5-25% EtOAc in hexane.
47. Askin, D.; Joe, D.; Reamer, R. A.; Volante, R. P.; Shinkai, I. J. Org. Chem. 1990, 55, 5451.
48. 2 = 13.4 Hz, 1H), 2.20 (s, 1H), 1.40-1.90 (m, 8H), 1.51 (s, 3H), 1.38 (s, 3H), 1.36 (s, 3H), 1-27 (s, 3H), 1.16 (s, 3H), 1.14 (s, 3H), 1.13 (s, 3H), 0.99 (s, 3H). MS mle: 598.5 (M + 1).