Synthesis of the reported structure of pogostol and a total synthesis of (±)-kessane without the use of protecting groups

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3309-3312

  Booker Milburn, Kevin I ^a   Jenkins, Helen ^a   Charmant, Jonathan P H ^a   Mohr, Peter ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; 4 HYDROXY 4 METHYL 2 CYCLOHEXENONE; ANTIEMETIC AGENT; IRON; KESSANE; POGOSTOL; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE;

EID: 0141744627     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035373u     Document Type: Article

References (21)

1. (a) Booker-Milburn, K. I. Synlett 1992, 809.
2. (b) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
3. (c) Booker-Milburn, K. I.; Barker, A.; Brailsford, W.; Cox, B.; Mansley, T. E. Tetrahedron 1998, 54, 15321.
4. Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545.
5. Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Ikeno, T.; Narasaka, K. Bull. Chem. Soc. Jpn. 1999, 72, 85.
6. Blake, A. J.; Highton, A. J.; Majid, T. N.; Simpkins, N. S. Org. Lett. 1999, 1787.
7. Lee, H. B.; Sung, M. J.; Blackstock, S. C.; Cha, J. K. J. Am. Chem. Soc. 2001, 123, 11322.
8. Booker-Milburn, K. I.; Cox, B.; Grady, M.; Halley, F.; Marrison, S. Tetrahedron Lett. 2000, 39, 4651.
9. Yang, Y.; Kinoshita, K.; Koyama, K.; Takahashi, K.; Tai, T.; Nunoura, Y. ; Watanabe, K. Phytomedicine 1999, 6, 89.
10. Weyerstahl, P.; Marschall, H.; Splittgerber, U.; Wolf, D. Flavour Fragr. J. 2000, 15, 153.
11. Fleischer, T. C.; Waigh R. D.; Waterman, P. G. J. Nat. Prod. 1997, 60, 1054.
12. Hikino, H.; Hikino, Y.; Takeshita, Y.; Shirata, K.; Takemoto, T. Chem. Pharm. Bull. 1967, 15, 321.
13. van Beek, T. A.; Lelyveld, G. P.; Gijsen, H. J. M. J. Essent. Oil. Res. 1993, 5, 169.
14. Csaky, A. G.; Mba, M.; Plumet, J. J. Org. Chem. 2001, 66, 9026.
15. Rao, C. G.; Kulkarni, S. U.; Brown, H. C. J. Organomet. Chem. 1979, 172, C20-C22.
16. Stepwise hydroboration and oxidation of the purified mixture of alcohols with DMP yielded the ketones 12 as a 1:1 mixture.
17. (a) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 3611.
18. (b) Clawson, L.; Buchwald, S. L.; Grubbs, R. H. Tetrahedron Lett. 1984, 25, 5733-5736.
19. 1 = 4.7% [for 2161 data with I > 2s(I)].
20. Gijsen, H. J. M.; Wijnberg, J. B. P. A.; Stork, G. A.; deGroot, A. Tetrahedron 1991, 47, 4409.
21. Reitz, A. B.; Nortey, S. O.; Maryanoff, B. E. J. Org. Chem. 1987, 52, 4191.