A General Solution to the Modular Synthesis of Polyketide Building Blocks by Kanemasa Hydroxy-Directed Nitrile Oxide Cycloadditions

Angewandte Chemie - International Edition

Volumn 40, Issue 11, 2001, Pages 2082-2085

  Bode, Jeffrey W ^a   Fraefel, Nina ^a   Muri, Dieter ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

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EID: 0001386311     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20010601)40:11<2082::AID-ANIE2082>3.0.CO;2-1     Document Type: Article

References (52)

1. For synthetic approaches to polyketides see: a) R. W. Hoffmann, Angew. Chem. 1987, 99, 503; Angew. Chem. Int. Ed. Engl. 1987, 26, 489; b) "The Total Synthesis of Macrolides": J. W. Bode, E. M. Carreira in The Chemical Synthesis of Natural Products (Ed.: K. J. Hale), Sheffield Academic Press, London, 2000, pp. 40-62.
2. For synthetic approaches to polyketides see: a) R. W. Hoffmann, Angew. Chem. 1987, 99, 503; Angew. Chem. Int. Ed. Engl. 1987, 26, 489; b) "The Total Synthesis of Macrolides": J. W. Bode, E. M. Carreira in The Chemical Synthesis of Natural Products (Ed.: K. J. Hale), Sheffield Academic Press, London, 2000, pp. 40-62.
3. For synthetic approaches to polyketides see: a) R. W. Hoffmann, Angew. Chem. 1987, 99, 503; Angew. Chem. Int. Ed. Engl. 1987, 26, 489; b) "The Total Synthesis of Macrolides": J. W. Bode, E. M. Carreira in The Chemical Synthesis of Natural Products (Ed.: K. J. Hale), Sheffield Academic Press, London, 2000, pp. 40-62.
4. For recent advances in bioengineering approaches to the modular synthesis of polyketides, see: a) D. E. Cane, C. T. Walsh, C. Khosla, Science 1998, 282, 63; b) L. Katz, Chem. Rev. 1997, 97, 2557; c) C. Khosla, Chem. Rev. 1997, 97, 2577.
5. For recent advances in bioengineering approaches to the modular synthesis of polyketides, see: a) D. E. Cane, C. T. Walsh, C. Khosla, Science 1998, 282, 63; b) L. Katz, Chem. Rev. 1997, 97, 2557; c) C. Khosla, Chem. Rev. 1997, 97, 2577.
6. For recent advances in bioengineering approaches to the modular synthesis of polyketides, see: a) D. E. Cane, C. T. Walsh, C. Khosla, Science 1998, 282, 63; b) L. Katz, Chem. Rev. 1997, 97, 2557; c) C. Khosla, Chem. Rev. 1997, 97, 2577.
7. For chiral auxiliary based approaches, see: D. A. Evans, J. V. Nelson, T. R. Taber, Top. Stereochem. 1982, 13, 1.
8. For substrate and reagent controlled aldol reactions to polypropionate subunits, see: I. Paterson, J. A. Channon, Tetrahedron Lett. 1992, 33, 797.
9. For reviews, see: a) "Stereoselective Aldol Reactions in the Synthesis of Polyketide Natural Products": I. Paterson, C. J. Cowden, D. J. Wallace in Modern Carbonyl Chemistry (Ed.: J. Otera), Wiley-VCH, Weinheim, 2000, pp. 249-297; b) C.J. Cowden, I. Paterson, Org. React. 1997, 51, 1.
10. For reviews, see: a) "Stereoselective Aldol Reactions in the Synthesis of Polyketide Natural Products": I. Paterson, C. J. Cowden, D. J. Wallace in Modern Carbonyl Chemistry (Ed.: J. Otera), Wiley-VCH, Weinheim, 2000, pp. 249-297; b) C.J. Cowden, I. Paterson, Org. React. 1997, 51, 1.
11. For the use of chiral allylation reagents in polyketide synthesis, see: a) "Recent Application of the Allylation Reaction to the Synthesis of Natural Products": S. R. Chemler, W. R. Roush in Modern Carbonyl Chemistry (Ed.: J. Otera), Wiley-VCH. Weinheim, 2000, pp. 404-490: b) R. W. Hoffman in Stereocontrolled Organic Synthesis (Ed.: B. M. Trost), Blackwell, Cambridge, 1994, pp. 259-274.
12. For the use of chiral allylation reagents in polyketide synthesis, see: a) "Recent Application of the Allylation Reaction to the Synthesis of Natural Products": S. R. Chemler, W. R. Roush in Modern Carbonyl Chemistry (Ed.: J. Otera), Wiley-VCH. Weinheim, 2000, pp. 404-490: b) R. W. Hoffman in Stereocontrolled Organic Synthesis (Ed.: B. M. Trost), Blackwell, Cambridge, 1994, pp. 259-274.
13. For chiral allenylmetal reagents, see: a) J. A. Marshall, S. Xie, J. Org. Chem. 1995, 60, 7230: b) J. A. Marshall, Z.-H. Lu, B. A. Johns, J. Org. Chem. 1998, 63, 817.
14. For chiral allenylmetal reagents, see: a) J. A. Marshall, S. Xie, J. Org. Chem. 1995, 60, 7230: b) J. A. Marshall, Z.-H. Lu, B. A. Johns, J. Org. Chem. 1998, 63, 817.
15. a) Epoxidc openings: D. Boschelli, T. Takemasa, Y. Nishitani, S. Masamune, Tetrahedron Lett. 1985, 26, 5239; b) hetero-Diels - Alder reactions: D. C. Myles, S. J. Danishefsky, Pure Appl. Chem. 1989, 61, 1235; c) hydroborations: M. R. Johnson, T. Nakata, Y. Kishi, Tetrahedron Lett. 1979, 20, 4343.
16. a) Epoxidc openings: D. Boschelli, T. Takemasa, Y. Nishitani, S. Masamune, Tetrahedron Lett. 1985, 26, 5239; b) hetero-Diels - Alder reactions: D. C. Myles, S. J. Danishefsky, Pure Appl. Chem. 1989, 61, 1235; c) hydroborations: M. R. Johnson, T. Nakata, Y. Kishi, Tetrahedron Lett. 1979, 20, 4343.
17. a) Epoxidc openings: D. Boschelli, T. Takemasa, Y. Nishitani, S. Masamune, Tetrahedron Lett. 1985, 26, 5239; b) hetero-Diels - Alder reactions: D. C. Myles, S. J. Danishefsky, Pure Appl. Chem. 1989, 61, 1235; c) hydroborations: M. R. Johnson, T. Nakata, Y. Kishi, Tetrahedron Lett. 1979, 20, 4343.
18. a) For an excellent overview, see: D. P. Curran, Adv. Cycloaddit. 1988, 1, 129; b) D. P. Curran, J. Am. Chem. Soc. 1982, 104, 4024; c) K. Torssell, O. Zeuthen. Acta Chem. Scand. Ser. B 1978, 32, 118.
19. a) For an excellent overview, see: D. P. Curran, Adv. Cycloaddit. 1988, 1, 129; b) D. P. Curran, J. Am. Chem. Soc. 1982, 104, 4024; c) K. Torssell, O. Zeuthen. Acta Chem. Scand. Ser. B 1978, 32, 118.
20. a) For an excellent overview, see: D. P. Curran, Adv. Cycloaddit. 1988, 1, 129; b) D. P. Curran, J. Am. Chem. Soc. 1982, 104, 4024; c) K. Torssell, O. Zeuthen. Acta Chem. Scand. Ser. B 1978, 32, 118.
21. For recent applications of convergent nitrile oxide cycloadditions, see: a) G. J. McGarvey, J. A. Mathys, K. J. Wilson, J., Org. Chem. 1996, 61, 5704; b) W. Zheng, J. A. DeMattei, J.-P. Wu, J. J.-W. Duan, L. R. Cook, H. Oinuma, Y. Kishi, J. Am. Chem. Soc. 1996, 118, 7946; c) J. W. Bode, E. M. Carreira, J. Am. Chem. Soc. 2001, 123, in press.
22. For recent applications of convergent nitrile oxide cycloadditions, see: a) G. J. McGarvey, J. A. Mathys, K. J. Wilson, J., Org. Chem. 1996, 61, 5704; b) W. Zheng, J. A. DeMattei, J.-P. Wu, J. J.-W. Duan, L. R. Cook, H. Oinuma, Y. Kishi, J. Am. Chem. Soc. 1996, 118, 7946; c) J. W. Bode, E. M. Carreira, J. Am. Chem. Soc. 2001, 123, in press.
23. For recent applications of convergent nitrile oxide cycloadditions, see: a) G. J. McGarvey, J. A. Mathys, K. J. Wilson, J., Org. Chem. 1996, 61, 5704; b) W. Zheng, J. A. DeMattei, J.-P. Wu, J. J.-W. Duan, L. R. Cook, H. Oinuma, Y. Kishi, J. Am. Chem. Soc. 1996, 118, 7946; c) J. W. Bode, E. M. Carreira, J. Am. Chem. Soc. 2001, 123, in press.
24. a) Grignard additions: D. P. Curran, J. Zheng, J. Chem. Soc. Perkins Trans. 1 1991, 2613; b) alkylation: V. Jäger, R. Schohe, E. F. Paulus, Tetrahedron Lett. 1983, 24, 5501; c) A. P. Kozikowski, A. K. Ghosh, J. Am. Chem. Soc. 1982, 104, 5788; d) Aldol addition: D. P. Curran, J.-C. Chao, J. Am. Chem. Soc. 1987, 109, 3037; e) A. Kamimura, S. Manumo, Tetrahedron Lett. 1990, 31, 5053.
25. a) Grignard additions: D. P. Curran, J. Zheng, J. Chem. Soc. Perkins Trans. 1 1991, 2613; b) alkylation: V. Jäger, R. Schohe, E. F. Paulus, Tetrahedron Lett. 1983, 24, 5501; c) A. P. Kozikowski, A. K. Ghosh, J. Am. Chem. Soc. 1982, 104, 5788; d) Aldol addition: D. P. Curran, J.-C. Chao, J. Am. Chem. Soc. 1987, 109, 3037; e) A. Kamimura, S. Manumo, Tetrahedron Lett. 1990, 31, 5053.
26. a) Grignard additions: D. P. Curran, J. Zheng, J. Chem. Soc. Perkins Trans. 1 1991, 2613; b) alkylation: V. Jäger, R. Schohe, E. F. Paulus, Tetrahedron Lett. 1983, 24, 5501; c) A. P. Kozikowski, A. K. Ghosh, J. Am. Chem. Soc. 1982, 104, 5788; d) Aldol addition: D. P. Curran, J.-C. Chao, J. Am. Chem. Soc. 1987, 109, 3037; e) A. Kamimura, S. Manumo, Tetrahedron Lett. 1990, 31, 5053.
27. a) Grignard additions: D. P. Curran, J. Zheng, J. Chem. Soc. Perkins Trans. 1 1991, 2613; b) alkylation: V. Jäger, R. Schohe, E. F. Paulus, Tetrahedron Lett. 1983, 24, 5501; c) A. P. Kozikowski, A. K. Ghosh, J. Am. Chem. Soc. 1982, 104, 5788; d) Aldol addition: D. P. Curran, J.-C. Chao, J. Am. Chem. Soc. 1987, 109, 3037; e) A. Kamimura, S. Manumo, Tetrahedron Lett. 1990, 31, 5053.
28. a) Grignard additions: D. P. Curran, J. Zheng, J. Chem. Soc. Perkins Trans. 1 1991, 2613; b) alkylation: V. Jäger, R. Schohe, E. F. Paulus, Tetrahedron Lett. 1983, 24, 5501; c) A. P. Kozikowski, A. K. Ghosh, J. Am. Chem. Soc. 1982, 104, 5788; d) Aldol addition: D. P. Curran, J.-C. Chao, J. Am. Chem. Soc. 1987, 109, 3037; e) A. Kamimura, S. Manumo, Tetrahedron Lett. 1990, 31, 5053.
29. a) C. J. Easton, C. M. M. Hughes, G. P. Savage, G. W. Simpson, Adv. Heterocycl. Chem. 1994, 60, 261; b) K. G. B. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Chemistry, VCH, Weinheim, 1988; c) A. P. Kozikowsi, Acc. Chem. Res. 1984, 17, 410.
30. a) C. J. Easton, C. M. M. Hughes, G. P. Savage, G. W. Simpson, Adv. Heterocycl. Chem. 1994, 60, 261; b) K. G. B. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Chemistry, VCH, Weinheim, 1988; c) A. P. Kozikowsi, Acc. Chem. Res. 1984, 17, 410.
31. a) C. J. Easton, C. M. M. Hughes, G. P. Savage, G. W. Simpson, Adv. Heterocycl. Chem. 1994, 60, 261; b) K. G. B. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Chemistry, VCH, Weinheim, 1988; c) A. P. Kozikowsi, Acc. Chem. Res. 1984, 17, 410.
32. S. Kanemasa, M. Nishiuchi, A. Kamimure, K. Hori, J. Am. Chem. Soc. 1994, 116, 2324.
33. 2O) is used for the in situ preparation of the magnesium alkoxides.
34. The synthesis of the corresponding aldehydes have been reported: a) A. Gaucher, J. Ollivier, J. Marguerite, R. Paugam, J. Salaün, Can. J. Chem. 1994, 72, 1312; b) in contrast to the corresponding aldehydes, which are unstable towards decomposition, we have found the oximes to be stable and amenable to prolonged storage.
35. The synthesis of the corresponding aldehydes have been reported: a) A. Gaucher, J. Ollivier, J. Marguerite, R. Paugam, J. Salaün, Can. J. Chem. 1994, 72, 1312; b) in contrast to the corresponding aldehydes, which are unstable towards decomposition, we have found the oximes to be stable and amenable to prolonged storage.
36. a) Several preparations of chiral olefins 3 and 4 have been reported in both enantiomeric forms. For our purposes they were prepared from enantiomerically pure 2-hydroxy-3-pentene, itself prepared by the method of Noyori et al.: K. Matsumura, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1997, 119, 8738; b) for another procedure, see O. Hamed, P. M. Henry, Organometallics 1997, 16, 4903.
37. a) Several preparations of chiral olefins 3 and 4 have been reported in both enantiomeric forms. For our purposes they were prepared from enantiomerically pure 2-hydroxy-3-pentene, itself prepared by the method of Noyori et al.: K. Matsumura, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1997, 119, 8738; b) for another procedure, see O. Hamed, P. M. Henry, Organometallics 1997, 16, 4903.
38. In all cases the resulting cycloadducts are formed syn to the existing hydroxy group. Although Kanemasa et al. have established that the cycloaddition typically proceeds in > 99:1 syn:anti diastereomer ratio, we have confirmed this sense of induction by X-ray diffraction analysis of a derivative of 6 and by a synthetic application of 12 (see ref. [11c]).
39. The use of the readily available enantiomers of allylic alcohols 3 and 4 provides a direct entry to the enantiomeric polypropionate building blocks.
40. For efforts towards iterative, solid-phase aldol approaches to polypropionates see: a) I. Paterson, J. P. Scott, J. Chem. Soc. Perkin Trans. 1 1999, 1003; b) I. Paterson, M. Donghi, K. Gerlach, Angew. Chem. 2000, 112, 3453; Angew. Chem. Int. Ed. 2000, 39, 3315.
41. For efforts towards iterative, solid-phase aldol approaches to polypropionates see: a) I. Paterson, J. P. Scott, J. Chem. Soc. Perkin Trans. 1 1999, 1003; b) I. Paterson, M. Donghi, K. Gerlach, Angew. Chem. 2000, 112, 3453; Angew. Chem. Int. Ed. 2000, 39, 3315.
42. For efforts towards iterative, solid-phase aldol approaches to polypropionates see: a) I. Paterson, J. P. Scott, J. Chem. Soc. Perkin Trans. 1 1999, 1003; b) I. Paterson, M. Donghi, K. Gerlach, Angew. Chem. 2000, 112, 3453; Angew. Chem. Int. Ed. 2000, 39, 3315.
43. The synthesis of related isoxazolines by enzymatic resolution on a solid support has been reported, see: J. A. López-Pelegrín, P. Wentworth, F. Sieber, W. A. Metz, K. D. Janda, J. Org. Chem. 2000, 65, 8527.
44. a) We speculate that the supposed tendency for alkyne-derived nitrile oxides to undergo dimerization or polymerization has precluded their prior use. b) Although oxime 13 is a readily prepared, known compound (L. P. Safronova, A. S. Medvedeva, N. S. Vyazankin, J. Gen. Chem. USSR Engl. Transl. 1983, 53, 1177) it is unstable towards prolonged storage.
45. a) We speculate that the supposed tendency for alkyne-derived nitrile oxides to undergo dimerization or polymerization has precluded their prior use. b) Although oxime 13 is a readily prepared, known compound (L. P. Safronova, A. S. Medvedeva, N. S. Vyazankin, J. Gen. Chem. USSR Engl. Transl. 1983, 53, 1177) it is unstable towards prolonged storage.
46. a) D. P. Curran, J. Am. Chem. Soc. 1983, 105, 5826;
47. b) D. P. Curran, S. A. Scanga, C. J. Fenk, J. Org. Chem. 1984, 49, 3474.
48. For recent examples, see: at I. Paterson, G. J. Florence, K. Gerlach, J. P. Scott, Angew. Chem. 2000, 112, 385; Angew. Chem. Int. Ed. 2000, 39, 277;
49. For recent examples, see: at I. Paterson, G. J. Florence, K. Gerlach, J. P. Scott, Angew. Chem. 2000, 112, 385; Angew. Chem. Int. Ed. 2000, 39, 277;
50. b) K. Tatsuda, Y. Koguchi, M. Kase, Bull. Chem. Soc. Jpn. 1988, 61, 2525;
51. c) C. Esteve, M. Ferreró, P. Romea, F. Urpí, J. Vilarrasa, Tetrahedron Lett. 1999, 40, 5083.
52. Iodide 17 was prepared by oxidation of 6 followed by Wittig olefination, deprotection, and iodide formation in 65% overall yield. Ketone 18 was prepared by oxidation of 5 in 91 % yield.