Total synthesis of herboxidiene/GEX 1A

Organic Letters

Volumn 9, Issue 16, 2007, Pages 3141-3143

  Yun, Zhang ^a   Panek, James S ^a  

^a Boston University

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; FATTY ALCOHOL; HERBOXIDIENE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; STREPTOMYCES; SYNTHESIS;

ANTINEOPLASTIC AGENTS; FATTY ALCOHOLS; MOLECULAR STRUCTURE; PYRANS; STEREOISOMERISM; STREPTOMYCES;

EID: 34547952285     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701427k     Document Type: Article

References (35)

1. Isaac, B. G.; Ayer, S. W.; Elliott, R. C.; Stonard, R. J. J. Org. Chem. 1992, 57, 7220.
2. Sakai, Y.; Yoshida, T.; Ochiai, K.; Uosaki, Y.; Saitoh, Y.; Tanaka, F.; Akiyama, T.; Akinaga, S.; Mizukami, T. J. Antibiot. 2002, 55, 855.
3. Sakai, Y.; Tsujita, T.; Akiyama, T.; Yoshida, T.; Mizukami, T.; Akinaga, S.; Horinouchi, S.; Yoshida, M.; Yoshida, M. J. Antibiot. 2002, 55, 863.
4. Edmunds, A. J. F.; Trueb, W.; Oppolzer, W.; Cowley, P. Tetrahedron 1997, 53, 2785.
5. Total synthesis, see: (a) Blakemore, P. R.; Kocieñski, P. J.; Morley, A.; Muir, K. J. Chem. Soc., Perkin Trans. 1 1999, 955.
6. (b) Banwell, M.; McLeod, M.; Premraj, R.; Simpson, G. Pure Appl. Chem. 2000, 72, 1631. Diastereomeric synthesis, see:
7. (c) Smith, N. D.; Kocieñski, P. J.; Street S. D. A. Synthesis 1996, 652. Fragment synthesis,
8. see: (d) Banwell, M. G.; Bui, C. T.; Simpson, G. W.; Watson, K. G. Chem. Commun. 1996, 723.
9. (e) Banwell, M. G.; Bui, C. T.; Hockless, D. C. R.; Simpson, G. W. J. Chem. Soc, Perkin Trans. 1 1997, 1261.
10. (f) Banwell, M. G.; Bui, C. T.; Simpson, G. W. J. Chem. Soc. Perkin Trans. 1 1998, 791. SAR studies,
11. see: (g) Edmunds, A. J. F.; Arnold, G.; Hagmann, L.; Schaffner, R.; Furienmeier, H. Med. Chem. Lett. 2000, 1365.
12. Huang, H.; Panek, J. S. J. Am. Chem. Soc. 2000, 122, 9836.
13. (a) Jain, N. F.; Takenaka, N.; Panek, J. S. J. Am. Chem. Soc. 1996, 118, 12475.
14. (b) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. 1985, 24, 1.
15. Lowe, J. T.; Panek, J. S. Org. Lett. 2005, 7, 1529.
16. (S)-Silyloxy acetal 13 was prepared in two steps from the commercially available (S)-ethyl lactate. See the Supporting Information for details.
17. Kirmse, W. Eur. J. Org. Chem. 2002, 2193.
18. Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecký, D.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496.
19. For preparation of LAB reagent, see ref 11.
20. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651.
21. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
22. (a) Mohamed, M.; Brook, M. A. Helv. Chim. Acta 2002, 85, 4165.
23. (b) Spino, C.; Gobdout, C. J. Am. Chem. Soc. 2003, 125, 12106.
24. For a review of hydroxyl-directed hydrogenation, see: Brown, J. M. Angew. Chem., Int. Ed. 1987, 26, 190.
25. For recent reports of Si-based X-couplings, see: (a) Denmark, S. E.; Neuville, L.; Christy, M. E. L.; Tymonko, S. A. J. Org. Chem. 2006, 71, 8500.
26. (b) Denmark, S. E.; Sweis, R. F.; Wehrli, D. J. Am. Chem. Soc. 2004, 126, 4865.
27. (c) Rendler, S.; Oestreich, M. Synthesis 2005, 1727.
28. (d) Spivey, A. C.; Gripton, C. J. G.; Hannah, J. Curr. Org. Synth. 2004, 7, 211.
29. (e) Denmark, S. E.; Liu, J. H. C. J. Am. Chem. Soc. 2007, 129, 3737.
30. For examples using benzyldimethylsilyl group in cross-coupling, see: (a) Trost, B. M.; Frederiksen, M. U.; Papillon, J. P. N.; Harrington, P. E.; Shin, S.; Shireman, B. T. J. Am. Chem. Soc. 2005, 127, 3666.
31. (b) Trost, B. M.; Machacek, M. R.; Ball, Z. T. Org. Lett. 2003, 5, 1895.
32. Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091.
33. (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
34. (b) Nakata, T.; Schmid, G.; Vranesic, B.; Okigawa, M.; Smith-Palmer, T.; Kishi, Y. J. Am. Chem. Soc. 1978, 100, 2933.
35. Martin, S. F.; Dodge, J. A.; Tetrahedron Lett. 1991, 32, 3017.