Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach

Organic Letters

Volumn 7, Issue 11, 2005, Pages 2261-2264

  Motozaki, Toru ^a   Sawamura, Kiyoto ^a   Suzuki, Akari ^a   Yoshida, Keigo ^a   Ueki, Tatsuo ^a   Ohara, Aiko ^a   Munakata, Ryosuke ^a   Takao, Ken Ichi ^a   Tadano, Kin Ichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; CARBON; MACROLIDE; MALIC ACID; TUBELACTOMICIN A; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; DIELS ALDER REACTION; MOLECULAR INTERACTION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

ACTINOMYCES; ANTI-BACTERIAL AGENTS; LACTONES; MACROLIDES; MALATES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 20444505606     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0507625     Document Type: Article

References (29)

1. (a) Igarashi, M.; Hayashi, C.; Homma, Y.; Hattori, S.; Kinoshita, N.; Hamada, M.; Takeuchi, T. J. Antibiot. 2000, 53, 1096-1101.
2. (b) Igarashi, M.; Nakamura H.; Naganawa, H.; Takeuchi, T. J. Antibiot. 2000, 53, 1102-1107.
3. For the total synthesis of (-)-chlorothricolide, see: (a) Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1994, 116, 6457-6458.
4. (b) Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1998, 120, 7411-7419.
5. For the total synthesis of (±)-24-O-methylchlorothricolide, see: (c) Takeda, K.; Igarashi, Y.; Okazaki, K.; Yoshii, E.; Yamaguchi, K. J. Org. Chem. 1990, 55, 3431-3434.
6. For the total synthesis of (+)-tetronolide, see: (d) Takeda, K.; Kawanishi, E.; Nakamura, H.; Yoshii, E. Tetrahedron Lett. 1991, 32, 4925-4928.
7. For the formal synthesis of (+)-tetronolide, see: (e) Roush, W. R.; Reilly, M. L.; Koyama. K.; Brown, B. B. J. Org. Chem. 1997, 62, 8708-8721.
8. For synthetic studies of superstolide A, see: (f) Roush, W. R.; Champoux, J. A.; Peterson, B. C. Tetrahedron Lett. 1996, 37, 8989-8992.
9. (g) Yu, W.; Zhang, Y.; Jin Z. Org. Lett. 2001, 3, 1447-1450.
10. (h) Zampella, A.; D'Auria, M. V. Tetrahedron: Asymmetry 2001, 12, 1543-1545.
11. (i) Roush, W. R.; Hertel, L.; Schnaderbeck, M. J.; Yakelis, N. A. Tetrahedron Lett. 2002, 43, 4885-4887.
12. (j) Yakelis, N. A.; Roush, W. R. J. Org. Chem. 2003, 68, 3838-3843.
13. For reviews on IMDA reactions, see: (a) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 153-550.
14. (b) Fallis, A. G. Acc. Chem. Res. 1999, 32, 464-474.
15. (c) Bear, B. R.; Sparks, S. M.; Shea, K. J. Angew. Chem., Int. Ed. 2001, 40, 820-849.
16. (d) Marsault, E.; Toró, A.; Nowak, P.; Deslongchamps, P. Tetrahedron 2001, 57, 4243-4260.
17. Wipf, P.; Uto, Y.; Yoshimura, S. Chem. Eur. J. 2002, 8, 1670-1681.
18. Motozaki, T.; Sawamura, K.; Suzuki, A.; Yoshida, K.; Ueki, T.; Ohara, A.; Munakata, R.; Takao, K.-i.; Tadano, K.-i. Org. Lett. 2005, 7, 2265-2268.
19. (a) Seebach, D,; Wasmuth, D. Helv. Chim. Acta 1980, 63, 197-200.
20. (b) Seebach, D.; Aebi, J.; Wasmuth, D. Org. Synth. 1984, 63, 109-120.
21. Owing to its highly polar nature, the reduction product was once acetylated. The peracetate was purified on silica gel and then deacetylated with a catalytic amount of NaOMe.
22. For the synthesis of enantiomeric 8, see: Morimoto, Y.; Mikami, A.; Kuwabe, S.; Shirahama, H. Tetrahedron: Asymmetry 1996, 7, 3371-3390.
23. (a) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
24. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
25. (c) Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538.
26. Phosphonate 13 was prepared from the known (E)-2-methyl-5- (trimethylsilyl)pent-2-en-4-yn-1-ol 26, which in turn was prepared from diethyl methylmalonate (24) via 25. For preparation of 25, see: Baker, R.; Castro, J. L. J. Chem. Soc., Perkin Trans. 1 1990, 47-65.
27. For preparation of 26, see: de Lera, A. R.; Iglesias, B.; Rodriguez, J.; Alvarez, R.; Lopez, S.; Villanueva, X.; Padros, E. J. Am. Chem. Soc. 1995, 117, 8220-8231.
28. 1H NMR analysis.
29. At this stage, the compound (not shown) derived from the minor exo-adduct of the IMDA reaction could be removed.