A Versatile A-ring Synthesis for Taxol

Synlett

Volumn 1996, Issue 12, 1996, Pages 1159-1161

  Toivola, Reijo J ^a   Koskinen, Ari M P ^a  

^a UNIVERSITY OF OULU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002777591     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5714     Document Type: Article

References (41)

1. Wani, M.C.; Taylor, H.L.; Wall, M.E.; Coggon, P.; McPhail, A.T. J. Am. Chem. Soc. 1971, 93, 2325-2327.
2. a) Holton, R.A.; Somoza, C.; Kim, H.-B.; Liang, F.; Biediger, R.J.; Boatman, P.D.; Shindo, M.; Smith, C.C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K.K.; Gentile, L.N.; Liu, J.H. J. Am. Chem. Soc.1994, 116, 1597-1598.
3. b) Holton, R.A.; Kim, H.-B.; Somoza, C.; Liang, F.; Biediger, R.J.; Boatman, P.D.; Shindo, M.; Smith, C.C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K.K.; Gentile, L.N.; Liu, J.H. J. Am. Chem. Soc. 1994, 116, 1599-1600.
4. a) Nicolaou, K.C.; Yang, Z.; Liu, J.J.; Ueno, H.; Nantermet, P.G.; Guy, R.K.; Claiborne, C.F.; Renaud, J.; Couladouros, E.A.; Paulvannan, K.; Sorensen, E.J. Nature 1994, 367, 630-634.
5. b) Nicolaou, K.C.; Nantermet, P.G.; Ueno, H.; Guy, R.K.; Couladouros, E.A.; Sorensen, E.J. J. Am. Chem. Soc. 1995, 117, 624-633.
6. c) Nicolaou, K.C.; Liu, J.-J.; Yang, Z.; Ueno, H.; Sorensen, E.J.; Claiborne, C.F.; Guy, R.K.; Hwang, C.-K.; Nakada, M.; Nantermet, P.G. J. Am. Chem. Soc. 1995, 117, 634-644.
7. d) Nicolaou, K.C.; Yang, Z.; Liu, J.-J.; Nantermet, P.G.; Claiborne, C.F.; Renaud, J.; Guy, R.K.; Shibayama, K. J. Am. Chem. Soc. 1995, 117, 645-652.
8. e) Nicolaou, K.C.; Ueno, H.; Liu, J.-J.; Nantermet, P.G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653-659.
9. a) Masters, J.J.; Link, J.T.; Snyder, L.B.; Young, W.B.; Danishefsky, S.J. Angew. Chem. Int. Ed. Engl. 1995, 34, 1723-1726.
10. b) Danishefsky, S.J.; Masters, J.J.; Young, W.B.; Link, J.T.; Snyder, L.B.; Magee, T.V.; Jung, D.K.; Isaacs, R.C.A.; Bornmann, W.G.; Alaimo, C.A.; Coburn, C.A.; Di Grandi, M.J. J. Am. Soc. 1996, 118, 2843-2859.
11. a) Koskinen, A.M.P.; Karvinen, E.K.; Siirilä, J.P. J. Chem. Soc., Chem. Commun. 1994, 21-22 and Koskinen, A.M.P.; Karvinen, E.K. In Enantioselective Synthesis of β-Amino Acids. (Juaristi, E., Ed.) VCH Publishers, in press.
12. a) Koskinen, A.M.P.; Karvinen, E.K.; Siirilä, J.P. J. Chem. Soc., Chem. Commun. 1994, 21-22 and Koskinen, A.M.P.; Karvinen, E.K. In Enantioselective Synthesis of β-Amino Acids. (Juaristi, E., Ed.) VCH Publishers, in press.
13. b) Karvinen, E.K.; Koskinen, A.M.P. Tetrahedron 1995, 51, 7555-7560.
14. c) Xia, Z.-Q.; Karvinen, E.; Koskinen, A. PCT Int. Appl. WO 96/00727.
15. As far as we know, our analysis is the first total substructure analysis published for the A-ring building block.
16. This because it is very likely that in the most efficient syntheses stereocenters at C3 and C8 will be available in the C-ring building block and the OH group at C13 is introduced after the construction of the ABCD skeleton. For a different approach, see Swindell, C.S.; Fan, W. Tetrahedron Lett. 1996, 37, 2321-2324.
17. The number of theoretical A-ring substructures is significantly larger than these three simple ones present More complex A-ring substructures will lead to complications, especially concerning stereochemistry at C3, C8, C13 and C1, and/or protection of the OH at C13.
18. a) Kress, M.H.; Ruel, R.; Miller, W.H.; Kishi, Y. Tetrahedron Lett. 1993, 34, 5999-6002.
19. b) Ibid 6003-6006.
20. a) Muller, B.; Delaloge, F.; den Hartog, M.; Férézou, J.-P.; Pancrazi, A.; Prunet, J.; Lallemand, J.-Y. Tetrahedron Lett. 1996, 37, 3313-3316.
21. b) In fact, Baylon and Hanna reported already last year the preparation of triflate 5, see Baylon, C.; Hanna, I. Tetrahedron Lett. 1995, 36, 6475-6478 and note 8 therein. Unfortunately, this note includes some typing, citating and/or factual inaccuracies.
22. The first step is known and the second briefly described, see a) Jacobson, B.M.; Soteropoulus, P.; Bahadori, S. J. Org. Chem. 1988, 53, 3247-3255 and Mori, K.; Mori, H. (submitted); Hopkins, M.; Overman, L.E. (checked) Org. Synth. 1990, 68, 56-60.
23. The first step is known and the second briefly described, see a) Jacobson, B.M.; Soteropoulus, P.; Bahadori, S. J. Org. Chem. 1988, 53, 3247-3255 and Mori, K.; Mori, H. (submitted); Hopkins, M.; Overman, L.E. (checked) Org. Synth. 1990, 68, 56-60.
24. b) Raju, N.; Rajagopalan, K.; Swaminathan, S. Tetrahedron Lett. 1980, 21, 1577-1580 and ref. 9a.
25. The first four steps discussed here were developed in this laboratory in 1994.
26. Adapted from literature processes, see 11a.
27. All compounds gave satisfactory spectral and analytical data.
28. Adapted from a literature process, see Andersen, N.H.; Uh, H.-s. Synth. Commun. 1973, 3, 125-128.
29. 2O as the catalyst, see 11b.
30. The corresponding ethylene ketal has also been prepared, see Tanaka, T. Bull. Chem. Soc. Jpn. 1967, 40, 233-234.
31. Earlier the corresponding ethylene ketal has been prepared from 2,2,4-trimethyl-1,3-cyclohexanedione, see Ito, M.; Masahara, R.; Tsukida, K. Tetrahedron Lett. 1977, 2767-2770 and Detering, J.; Martin, H.-D. Angew. Chem. 1988, 100, 714-716. Further, 2,2,4-trimethyl-1,3-cyclohexanedione was prepared from 2-methyl-3-pentanone and acryloyl chloride, see Hargreaves, J.R.; Hickmont, P.W.; Hopkins, B.J. J. Chem. Soc. C 1968, 2599-2603.
32. Earlier the corresponding ethylene ketal has been prepared from 2,2,4-trimethyl-1,3-cyclohexanedione, see Ito, M.; Masahara, R.; Tsukida, K. Tetrahedron Lett. 1977, 2767-2770 and Detering, J.; Martin, H.-D. Angew. Chem. 1988, 100, 714-716. Further, 2,2,4-trimethyl-1,3-cyclohexanedione was prepared from 2-methyl-3-pentanone and acryloyl chloride, see Hargreaves, J.R.; Hickmont, P.W.; Hopkins, B.J. J. Chem. Soc. C 1968, 2599-2603.
33. Earlier the corresponding ethylene ketal has been prepared from 2,2,4-trimethyl-1,3-cyclohexanedione, see Ito, M.; Masahara, R.; Tsukida, K. Tetrahedron Lett. 1977, 2767-2770 and Detering, J.; Martin, H.-D. Angew. Chem. 1988, 100, 714-716. Further, 2,2,4-trimethyl-1,3-cyclohexanedione was prepared from 2-methyl-3-pentanone and acryloyl chloride, see Hargreaves, J.R.; Hickmont, P.W.; Hopkins, B.J. J. Chem. Soc. C 1968, 2599-2603.
34. An adaptation of a literature process, see McMurry, J.E.; Scott, W.J. Tetrahedron Lett. 1983, 24, 979-982.
35. For the corresponding ethylene ketal, see Queneau, Y.; Krol, W.J., Bornmann, W.G.; Danishefsky, S.J. J. Org. Chem. 1992, 57, 4043-4047.
36. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1985, 26, 1109-1112.
37. Grushin, V.V.; Alper, H. J. Am. Chem. Soc. 1995, 117, 4305-4315 and references cited therein.
38. Skoda-Foldes, R.; Kollar, L.; Csakai, Z. Young Organic Chemists' Workshop on "Selective Synthesis", COST D2, 16-19th Septemper 1995, Budapest, Hungary.
39. Coulson, D.R. Inorg. Synth. 1972, 13, 121; Hegedus, L.S. in Organometallics in Synthesis - A Manual. (Schlosser. M., Ed.) John Wiley & Sons Ltd, Chihester, 1994, p 448.
40. Coulson, D.R. Inorg. Synth. 1972, 13, 121; Hegedus, L.S. in Organometallics in Synthesis - A Manual. (Schlosser. M., Ed.) John Wiley & Sons Ltd, Chihester, 1994, p 448.
41. Detailed mechanistic studies of both Pd-reactions are underway, and will be reported in due course.