Taxane diterpenes 1. Control of relative and absolute stereochemistry in intramolecular pyrylium ylide-alkene cyclizations for the synthesis of taxol precursors

Tetrahedron

Volumn 52, Issue 45, 1996, Pages 14081-14102

  Bauta, William E ^a   Booth, John ^a   Bos, Mary E ^a   DeLuca, Mark ^a   Diorazio, Louis ^a   Donohoe, Timothy J ^a   Frost, Christopher ^a   Magnus, Nicholas ^a   Magnus, Philip ^a   Mendoza, José ^a   Pye, Philip ^a   Tarrant, James G ^a   Thom, Stephen ^a   Ujjainwalla, Feroze ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 16044370366     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00867-8     Document Type: Article

References (62)

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46. 11. Tamaru, Y.; Ochai, H.; Nakamura, T.; Yoshida, Z. Org. Synth. 1988, 67, 98. Tamaru, Y.; Ochiai, H.; Nakamura, T.; Tsubaki, K.; Yoshida, Z. Tetrahedron Lett. 1985, 26, 5559. Tamaru, Y.; Yasui, K.; Takanabe, H.; Tanaka, S.; Fugami, K. Angew. Chem. Int. Ed. Engl. 1992, 31, 645. Tamaru, Y.; Tamura, M.; Kochi, J. Synthesis 1971, 303. Ochiai, H.; Tamaru, Y.; Tsubaki, K.; Yoshida, Z. J. Org. Chem. 1987, 52, 4418.
47. 11. Tamaru, Y.; Ochai, H.; Nakamura, T.; Yoshida, Z. Org. Synth. 1988, 67, 98. Tamaru, Y.; Ochiai, H.; Nakamura, T.; Tsubaki, K.; Yoshida, Z. Tetrahedron Lett. 1985, 26, 5559. Tamaru, Y.; Yasui, K.; Takanabe, H.; Tanaka, S.; Fugami, K. Angew. Chem. Int. Ed. Engl. 1992, 31, 645. Tamaru, Y.; Tamura, M.; Kochi, J. Synthesis 1971, 303. Ochiai, H.; Tamaru, Y.; Tsubaki, K.; Yoshida, Z. J. Org. Chem. 1987, 52, 4418.
48. 11. Tamaru, Y.; Ochai, H.; Nakamura, T.; Yoshida, Z. Org. Synth. 1988, 67, 98. Tamaru, Y.; Ochiai, H.; Nakamura, T.; Tsubaki, K.; Yoshida, Z. Tetrahedron Lett. 1985, 26, 5559. Tamaru, Y.; Yasui, K.; Takanabe, H.; Tanaka, S.; Fugami, K. Angew. Chem. Int. Ed. Engl. 1992, 31, 645. Tamaru, Y.; Tamura, M.; Kochi, J. Synthesis 1971, 303. Ochiai, H.; Tamaru, Y.; Tsubaki, K.; Yoshida, Z. J. Org. Chem. 1987, 52, 4418.
49. 11. Tamaru, Y.; Ochai, H.; Nakamura, T.; Yoshida, Z. Org. Synth. 1988, 67, 98. Tamaru, Y.; Ochiai, H.; Nakamura, T.; Tsubaki, K.; Yoshida, Z. Tetrahedron Lett. 1985, 26, 5559. Tamaru, Y.; Yasui, K.; Takanabe, H.; Tanaka, S.; Fugami, K. Angew. Chem. Int. Ed. Engl. 1992, 31, 645. Tamaru, Y.; Tamura, M.; Kochi, J. Synthesis 1971, 303. Ochiai, H.; Tamaru, Y.; Tsubaki, K.; Yoshida, Z. J. Org. Chem. 1987, 52, 4418.
50. 11. Tamaru, Y.; Ochai, H.; Nakamura, T.; Yoshida, Z. Org. Synth. 1988, 67, 98. Tamaru, Y.; Ochiai, H.; Nakamura, T.; Tsubaki, K.; Yoshida, Z. Tetrahedron Lett. 1985, 26, 5559. Tamaru, Y.; Yasui, K.; Takanabe, H.; Tanaka, S.; Fugami, K. Angew. Chem. Int. Ed. Engl. 1992, 31, 645. Tamaru, Y.; Tamura, M.; Kochi, J. Synthesis 1971, 303. Ochiai, H.; Tamaru, Y.; Tsubaki, K.; Yoshida, Z. J. Org. Chem. 1987, 52, 4418.
51. 12. Jubert, C.; Knochel, P. J. Org. Chem. 1992, 57, 5425.
52. 13. Luche, J. L. J. Am. Chem. Soc. 1978, 100, 2226.
53. 14. The compound i was converted into ii by conjugate addition of the appropriate vinyl lithium species, and acid hydrolysis followed by treatment with KCN resulted in the aldol product iii rather than cyanohydrin formation. (equation presented)
54. 15. MM2 calculations support the notion that the major diastereomer formed in these cyclizations is the least sterically strained.
55. 16. Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925. Jones, T. K.; Mohan, J. J.; Xavier, L. C.; Blacklock, T. J.; Mathre, D. J.; Sohar, P.; Jones, E. T. T.; Reamer, R. A.; Roberts, F. E.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 763.
56. 16. Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925. Jones, T. K.; Mohan, J. J.; Xavier, L. C.; Blacklock, T. J.; Mathre, D. J.; Sohar, P.; Jones, E. T. T.; Reamer, R. A.; Roberts, F. E.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 763.
57. 17. We initially used the (S) catalyst and converted the resulting alcohol into iv, whose structure and absolute stereochemistry was established by X-ray crystallography. (equation presented)
58. 18. Evans, D. A.; Ennis, M. D.; Le, T.; Mandel, N.; Mandel, G. J. Am. Chem. Soc. 1984, 106, 1154. Gage J, R.; Evans, D. A. Org. Synth. 1989, 68, 77, and 83. Evans, D. A.; Takacs, J. M.; McGee, L. R.; Ennis, M. D.; Mathre D. J.; Bartroli, J. Pure and App. Chem. 1981, 53, 1109.
59. 18. Evans, D. A.; Ennis, M. D.; Le, T.; Mandel, N.; Mandel, G. J. Am. Chem. Soc. 1984, 106, 1154. Gage J, R.; Evans, D. A. Org. Synth. 1989, 68, 77, and 83. Evans, D. A.; Takacs, J. M.; McGee, L. R.; Ennis, M. D.; Mathre D. J.; Bartroli, J. Pure and App. Chem. 1981, 53, 1109.
60. 18. Evans, D. A.; Ennis, M. D.; Le, T.; Mandel, N.; Mandel, G. J. Am. Chem. Soc. 1984, 106, 1154. Gage J, R.; Evans, D. A. Org. Synth. 1989, 68, 77, and 83. Evans, D. A.; Takacs, J. M.; McGee, L. R.; Ennis, M. D.; Mathre D. J.; Bartroli, J. Pure and App. Chem. 1981, 53, 1109.
61. 19. The absolute stereochemistry of 52 was determined by an X-ray structure of a camphanate ester derivative.
62. 20. Fuson, R. C.; Arnold, R. T.; Cooke, H. G. Jr. J. Am. Chem. Soc. 1938, 60, 2272.