1,8-Stereocontrol by 1,5-induction using an allylstannane followed by Ireland-Claisen rearrangement: Diastereoselective total synthesis of (±)- patulolide C

Tetrahedron Letters

Volumn 40, Issue 3, 1999, Pages 471-474

  Dorling, E Kate ^a   Thomas, Eric J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; PATULOLIDE C; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG STRUCTURE; ISOMERISM; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033555234     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02427-7     Document Type: Article

References (21)

1. Thomas, E. J. Chem. Commun. 1997, 411-418.
2. McNeill, A. H.; Thomas, E. J. Synthesis 1994, 322-334.
3. Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897-5898; Ireland, R. E.; Wipf, P.; Armstrong III, J. D. J. Org. Chem. 1991, 56, 650-657; Zeigler, F. E. Chem. Rev. 1988, 88, 1423-1452.
4. Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897-5898; Ireland, R. E.; Wipf, P.; Armstrong III, J. D. J. Org. Chem. 1991, 56, 650-657; Zeigler, F. E. Chem. Rev. 1988, 88, 1423-1452.
5. Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897-5898; Ireland, R. E.; Wipf, P.; Armstrong III, J. D. J. Org. Chem. 1991, 56, 650-657; Zeigler, F. E. Chem. Rev. 1988, 88, 1423-1452.
6. Rodpnaya, D.; Sekiguchi, J.; Yamada, Y. J. Antibiot. 1986, 39, 629.
7. For other syntheses of patulolide C see: Mori, K.; Sakai, T. Annalen, 1988, 13-17; Thijs, L.; Egenberger, D. M.; Zwanenburg, B. Tetrahedron Lett. 1989, 30, 2153-2156; Yang, H.; Kuroda, H.; Miyashita, M.; Irie, H. Chem. Pharm. Bull. 1992, 40, 1616-1618; Leemhuis, F. M. C.; Thijs, L.; Zwanenburg, B. J. Org. Chem. 1993, 58, 7170-7179; Takano, S.; Murakami, T.; Samizu, K.; Ogasawara, K. Hetereocycles 1994, 39, 67-72.
8. For other syntheses of patulolide C see: Mori, K.; Sakai, T. Annalen, 1988, 13-17; Thijs, L.; Egenberger, D. M.; Zwanenburg, B. Tetrahedron Lett. 1989, 30, 2153-2156; Yang, H.; Kuroda, H.; Miyashita, M.; Irie, H. Chem. Pharm. Bull. 1992, 40, 1616-1618; Leemhuis, F. M. C.; Thijs, L.; Zwanenburg, B. J. Org. Chem. 1993, 58, 7170-7179; Takano, S.; Murakami, T.; Samizu, K.; Ogasawara, K. Hetereocycles 1994, 39, 67-72.
9. For other syntheses of patulolide C see: Mori, K.; Sakai, T. Annalen, 1988, 13-17; Thijs, L.; Egenberger, D. M.; Zwanenburg, B. Tetrahedron Lett. 1989, 30, 2153-2156; Yang, H.; Kuroda, H.; Miyashita, M.; Irie, H. Chem. Pharm. Bull. 1992, 40, 1616-1618; Leemhuis, F. M. C.; Thijs, L.; Zwanenburg, B. J. Org. Chem. 1993, 58, 7170-7179; Takano, S.; Murakami, T.; Samizu, K.; Ogasawara, K. Hetereocycles 1994, 39, 67-72.
10. For other syntheses of patulolide C see: Mori, K.; Sakai, T. Annalen, 1988, 13-17; Thijs, L.; Egenberger, D. M.; Zwanenburg, B. Tetrahedron Lett. 1989, 30, 2153-2156; Yang, H.; Kuroda, H.; Miyashita, M.; Irie, H. Chem. Pharm. Bull. 1992, 40, 1616-1618; Leemhuis, F. M. C.; Thijs, L.; Zwanenburg, B. J. Org. Chem. 1993, 58, 7170-7179; Takano, S.; Murakami, T.; Samizu, K.; Ogasawara, K. Hetereocycles 1994, 39, 67-72.
11. For other syntheses of patulolide C see: Mori, K.; Sakai, T. Annalen, 1988, 13-17; Thijs, L.; Egenberger, D. M.; Zwanenburg, B. Tetrahedron Lett. 1989, 30, 2153-2156; Yang, H.; Kuroda, H.; Miyashita, M.; Irie, H. Chem. Pharm. Bull. 1992, 40, 1616-1618; Leemhuis, F. M. C.; Thijs, L.; Zwanenburg, B. J. Org. Chem. 1993, 58, 7170-7179; Takano, S.; Murakami, T.; Samizu, K.; Ogasawara, K. Hetereocycles 1994, 39, 67-72.
12. Bartlett, P. A.; Tanzella, D. J.; Barstow, J. F. J. Org. Chem. 1982, 47, 3941-3945; Burke, S. D.; Fobare, W. F.; Pacofsky, G. J. J. Org. Chem. 1983, 48, 5221-5228; Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, J. A.; Rossanao, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889-3901.
13. Bartlett, P. A.; Tanzella, D. J.; Barstow, J. F. J. Org. Chem. 1982, 47, 3941-3945; Burke, S. D.; Fobare, W. F.; Pacofsky, G. J. J. Org. Chem. 1983, 48, 5221-5228; Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, J. A.; Rossanao, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889-3901.
14. Bartlett, P. A.; Tanzella, D. J.; Barstow, J. F. J. Org. Chem. 1982, 47, 3941-3945; Burke, S. D.; Fobare, W. F.; Pacofsky, G. J. J. Org. Chem. 1983, 48, 5221-5228; Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, J. A.; Rossanao, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889-3901.
15. + + 18, 100%) and 412 (13).
16. Ratio from addition of trimethylsilyl chloride to preformed lithium enolate of ester 11 in THF.
17. Ratio from addition of lithium hexamethyldisilazide to a mixture of ester 15 and trimethylsilyl chloride in solution in THF
18. 3.
19. + + 1, 32).
20. Dorling, E. K.; Thomas, A. P.; Thomas, E. J. Tetrahedron Lett. 1999, 40, 475-476.
21. Moffatt, E. M.; Thomas, E. J. Tetrahedron, in print.