The total synthesis of scytophycin C. Part 1: Stereocontrolled synthesis of the C1-C32 protected seco acid

Tetrahedron

Volumn 54, Issue 39, 1998, Pages 11935-11954

  Paterson, Ian ^a   Yeung, Kap Sun ^a   Watson, Christine ^a   Ward, Richard A ^a   Wallace, Paul A ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; BARIUM; BORON; HYDROXIDE; MACROLIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032563999     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)83050-0     Document Type: Article

References (82)

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41. 20D -12.2 (c 1.6, MeOH)) of the homoallylic alcohol 15 matched with those reported in this paper. (b) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 5919. (c) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293.
42. 20D -12.2 (c 1.6, MeOH)) of the homoallylic alcohol 15 matched with those reported in this paper. (b) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 5919. (c) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293.
43. 2O, 0 → 20 °C; (ii) MeNHOMe•HCl, i-PrMgCl, THF, -5 °C; (iii) DIBAL, THF, -78 °C. It was used without purification in the crotylboration reaction. For other methods of preparation of this aldehyde and comparison spectroscopic data, see: (a) Meyers, A. I.; Babiak, K. A.; Campbell, A. L.; Comins, D. L.; Fleming, M. P.; Henning, R.; Heuschmann, M.; Hudspeth, J. P.; Kane, J. M.; Reider, P. J.; Roland, D. M.; Shimizu, K.; Tomioka, K.; Walkup, R. D. J. Am. Chem. Soc. 1983, 105, 5015. (b) Jackson, R. F. W.; Sutler, M. A.; Seebach, D. Liebigs Ann. Chem. 1985, 2313. (c) Hosokawa, T.; Yamanaka, T.; Itotani, M.; Murahashi, S.-I. J. Org. Chem. 1995, 60, 6159. The corresponding ethyl ketone (S)-17 was obtained in 89% overall yield by Grignard addition (EtMgBr, THF, 0 °C, 1 h) to the intermediate Weinreb amide rather than DIBAL reduction, see ref 14a. For step (11), see: (d) Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
44. 2O, 0 → 20 °C; (ii) MeNHOMe•HCl, i-PrMgCl, THF, -5 °C; (iii) DIBAL, THF, -78 °C. It was used without purification in the crotylboration reaction. For other methods of preparation of this aldehyde and comparison spectroscopic data, see: (a) Meyers, A. I.; Babiak, K. A.; Campbell, A. L.; Comins, D. L.; Fleming, M. P.; Henning, R.; Heuschmann, M.; Hudspeth, J. P.; Kane, J. M.; Reider, P. J.; Roland, D. M.; Shimizu, K.; Tomioka, K.; Walkup, R. D. J. Am. Chem. Soc. 1983, 105, 5015. (b) Jackson, R. F. W.; Sutler, M. A.; Seebach, D. Liebigs Ann. Chem. 1985, 2313. (c) Hosokawa, T.; Yamanaka, T.; Itotani, M.; Murahashi, S.-I. J. Org. Chem. 1995, 60, 6159. The corresponding ethyl ketone (S)-17 was obtained in 89% overall yield by Grignard addition (EtMgBr, THF, 0 °C, 1 h) to the intermediate Weinreb amide rather than DIBAL reduction, see ref 14a. For step (11), see: (d) Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
45. 2O, 0 → 20 °C; (ii) MeNHOMe•HCl, i-PrMgCl, THF, -5 °C; (iii) DIBAL, THF, -78 °C. It was used without purification in the crotylboration reaction. For other methods of preparation of this aldehyde and comparison spectroscopic data, see: (a) Meyers, A. I.; Babiak, K. A.; Campbell, A. L.; Comins, D. L.; Fleming, M. P.; Henning, R.; Heuschmann, M.; Hudspeth, J. P.; Kane, J. M.; Reider, P. J.; Roland, D. M.; Shimizu, K.; Tomioka, K.; Walkup, R. D. J. Am. Chem. Soc. 1983, 105, 5015. (b) Jackson, R. F. W.; Sutler, M. A.; Seebach, D. Liebigs Ann. Chem. 1985, 2313. (c) Hosokawa, T.; Yamanaka, T.; Itotani, M.; Murahashi, S.-I. J. Org. Chem. 1995, 60, 6159. The corresponding ethyl ketone (S)-17 was obtained in 89% overall yield by Grignard addition (EtMgBr, THF, 0 °C, 1 h) to the intermediate Weinreb amide rather than DIBAL reduction, see ref 14a. For step (11), see: (d) Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
46. 2O, 0 → 20 °C; (ii) MeNHOMe•HCl, i-PrMgCl, THF, -5 °C; (iii) DIBAL, THF, -78 °C. It was used without purification in the crotylboration reaction. For other methods of preparation of this aldehyde and comparison spectroscopic data, see: (a) Meyers, A. I.; Babiak, K. A.; Campbell, A. L.; Comins, D. L.; Fleming, M. P.; Henning, R.; Heuschmann, M.; Hudspeth, J. P.; Kane, J. M.; Reider, P. J.; Roland, D. M.; Shimizu, K.; Tomioka, K.; Walkup, R. D. J. Am. Chem. Soc. 1983, 105, 5015. (b) Jackson, R. F. W.; Sutler, M. A.; Seebach, D. Liebigs Ann. Chem. 1985, 2313. (c) Hosokawa, T.; Yamanaka, T.; Itotani, M.; Murahashi, S.-I. J. Org. Chem. 1995, 60, 6159. The corresponding ethyl ketone (S)-17 was obtained in 89% overall yield by Grignard addition (EtMgBr, THF, 0 °C, 1 h) to the intermediate Weinreb amide rather than DIBAL reduction, see ref 14a. For step (11), see: (d) Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
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49. For examples of applications to other polyketide natural products, see: (a) Paterson, I; Perkins, M. V. J. Am. Chem. Soc. 1993, 115, 1608. (b) Paterson, I.; Tillyer, R. D.; Ryan, G. R. Tetrahedron Lett. 1993, 34, 4389. (c) Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (d) Paterson, I.; Wren, S. P. J. Chem. Soc., Chem. Commun. 1993, 1790. (e) Paterson, L; Franklin, A. S. Tetrahedron Lett. 1994, 35, 6925. (f) Paterson, I.; Schlapbach, A. Synlett 1995, 498. (g) Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811. (h) Paterson, I.; Man, J. Tetrahedron Lett. 1997, 38, 695.
50. For examples of applications to other polyketide natural products, see: (a) Paterson, I; Perkins, M. V. J. Am. Chem. Soc. 1993, 115, 1608. (b) Paterson, I.; Tillyer, R. D.; Ryan, G. R. Tetrahedron Lett. 1993, 34, 4389. (c) Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (d) Paterson, I.; Wren, S. P. J. Chem. Soc., Chem. Commun. 1993, 1790. (e) Paterson, L; Franklin, A. S. Tetrahedron Lett. 1994, 35, 6925. (f) Paterson, I.; Schlapbach, A. Synlett 1995, 498. (g) Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811. (h) Paterson, I.; Man, J. Tetrahedron Lett. 1997, 38, 695.
51. For examples of applications to other polyketide natural products, see: (a) Paterson, I; Perkins, M. V. J. Am. Chem. Soc. 1993, 115, 1608. (b) Paterson, I.; Tillyer, R. D.; Ryan, G. R. Tetrahedron Lett. 1993, 34, 4389. (c) Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (d) Paterson, I.; Wren, S. P. J. Chem. Soc., Chem. Commun. 1993, 1790. (e) Paterson, L; Franklin, A. S. Tetrahedron Lett. 1994, 35, 6925. (f) Paterson, I.; Schlapbach, A. Synlett 1995, 498. (g) Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811. (h) Paterson, I.; Man, J. Tetrahedron Lett. 1997, 38, 695.
52. For examples of applications to other polyketide natural products, see: (a) Paterson, I; Perkins, M. V. J. Am. Chem. Soc. 1993, 115, 1608. (b) Paterson, I.; Tillyer, R. D.; Ryan, G. R. Tetrahedron Lett. 1993, 34, 4389. (c) Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (d) Paterson, I.; Wren, S. P. J. Chem. Soc., Chem. Commun. 1993, 1790. (e) Paterson, L; Franklin, A. S. Tetrahedron Lett. 1994, 35, 6925. (f) Paterson, I.; Schlapbach, A. Synlett 1995, 498. (g) Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811. (h) Paterson, I.; Man, J. Tetrahedron Lett. 1997, 38, 695.
53. For examples of applications to other polyketide natural products, see: (a) Paterson, I; Perkins, M. V. J. Am. Chem. Soc. 1993, 115, 1608. (b) Paterson, I.; Tillyer, R. D.; Ryan, G. R. Tetrahedron Lett. 1993, 34, 4389. (c) Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (d) Paterson, I.; Wren, S. P. J. Chem. Soc., Chem. Commun. 1993, 1790. (e) Paterson, L; Franklin, A. S. Tetrahedron Lett. 1994, 35, 6925. (f) Paterson, I.; Schlapbach, A. Synlett 1995, 498. (g) Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811. (h) Paterson, I.; Man, J. Tetrahedron Lett. 1997, 38, 695.
54. For examples of applications to other polyketide natural products, see: (a) Paterson, I; Perkins, M. V. J. Am. Chem. Soc. 1993, 115, 1608. (b) Paterson, I.; Tillyer, R. D.; Ryan, G. R. Tetrahedron Lett. 1993, 34, 4389. (c) Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (d) Paterson, I.; Wren, S. P. J. Chem. Soc., Chem. Commun. 1993, 1790. (e) Paterson, L; Franklin, A. S. Tetrahedron Lett. 1994, 35, 6925. (f) Paterson, I.; Schlapbach, A. Synlett 1995, 498. (g) Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811. (h) Paterson, I.; Man, J. Tetrahedron Lett. 1997, 38, 695.
55. For examples of applications to other polyketide natural products, see: (a) Paterson, I; Perkins, M. V. J. Am. Chem. Soc. 1993, 115, 1608. (b) Paterson, I.; Tillyer, R. D.; Ryan, G. R. Tetrahedron Lett. 1993, 34, 4389. (c) Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (d) Paterson, I.; Wren, S. P. J. Chem. Soc., Chem. Commun. 1993, 1790. (e) Paterson, L; Franklin, A. S. Tetrahedron Lett. 1994, 35, 6925. (f) Paterson, I.; Schlapbach, A. Synlett 1995, 498. (g) Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811. (h) Paterson, I.; Man, J. Tetrahedron Lett. 1997, 38, 695.
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