A unified total synthesis of the immunomodulators (-)-rapamycin and (-)-27-demethoxyrapamycin: Construction of the C(21-42) perimeters

Journal of the American Chemical Society

Volumn 119, Issue 5, 1997, Pages 947-961

  Smith III, Amos B ^a   Condon, Stephen M ^a   McCauley, John A ^a   Leazer Jr , Johnnie L ^a   Leahy, James W ^a   Maleczka Jr , Robert E ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEMETHOXYRAPAMYCIN; IMMUNOMODULATING AGENT; RAPAMYCIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031018562     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963066w     Document Type: Article

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33. Other natural congeners of 1 include (a) 27-desmethylrapamycm: Ondeyka, J.; Hensens, O.; Liesch, J. U.S. Patent 5,091,389, 1992. (b) 16,27-bis(desmethyl)rapamycin: Byrne, K.; Goegelman, R. T.; Hensens, O.; Kaplan, L.; Liesch, J. M. U.S. Patent 5,093,338, 1992. 2-norrapamycin: Chan, J. A.; Gerber, R.; Johnson, R. K.; Luengo, J. I. U.S. Patent 5,162,333, May 26, 1994.
34. Other natural congeners of 1 include (a) 27-desmethylrapamycm: Ondeyka, J.; Hensens, O.; Liesch, J. U.S. Patent 5,091,389, 1992. (b) 16,27-bis(desmethyl)rapamycin: Byrne, K.; Goegelman, R. T.; Hensens, O.; Kaplan, L.; Liesch, J. M. U.S. Patent 5,093,338, 1992. 2-norrapamycin: Chan, J. A.; Gerber, R.; Johnson, R. K.; Luengo, J. I. U.S. Patent 5,162,333, May 26, 1994.
35. Other natural congeners of 1 include (a) 27-desmethylrapamycm: Ondeyka, J.; Hensens, O.; Liesch, J. U.S. Patent 5,091,389, 1992. (b) 16,27-bis(desmethyl)rapamycin: Byrne, K.; Goegelman, R. T.; Hensens, O.; Kaplan, L.; Liesch, J. M. U.S. Patent 5,093,338, 1992. (c) 2-norrapamycin: Chan, J. A.; Gerber, R.; Johnson, R. K.; Luengo, J. I. U.S. Patent 5,162,333, May 26, 1994.
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40. Synthetic approaches to 1: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643. (b) Eshelman, J. E.; Epps, J. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 749. Sin, N.; Kallmerten, J. Ibid. 1993, 34, 753. Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (e) Rao, A. V. R.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111. (f) Ny, S.; Kallmerten, J. Ibid. 1993, 34, 753. (g) Pattenden, G.; Tankard, M.; Cherry, P. C. Ibid. 1993, 34, 2677. (h) Anderson, J. C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2087. Kouklousky, C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2091. (j) Ley, S. V.; Norman, J.; Pinel, C. Ibid. 1994, 35, 2095. (k) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77. (1) Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835. Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
41. Synthetic approaches to 1: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643. (b) Eshelman, J. E.; Epps, J. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 749. Sin, N.; Kallmerten, J. Ibid. 1993, 34, 753. Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (e) Rao, A. V. R.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111. (f) Ny, S.; Kallmerten, J. Ibid. 1993, 34, 753. (g) Pattenden, G.; Tankard, M.; Cherry, P. C. Ibid. 1993, 34, 2677. (h) Anderson, J. C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2087. Kouklousky, C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2091. (j) Ley, S. V.; Norman, J.; Pinel, C. Ibid. 1994, 35, 2095. (k) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77. (1) Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835. Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
42. Synthetic approaches to 1: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643. (b) Eshelman, J. E.; Epps, J. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 749. (c) Sin, N.; Kallmerten, J. Ibid. 1993, 34, 753. Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (e) Rao, A. V. R.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111. (f) Ny, S.; Kallmerten, J. Ibid. 1993, 34, 753. (g) Pattenden, G.; Tankard, M.; Cherry, P. C. Ibid. 1993, 34, 2677. (h) Anderson, J. C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2087. Kouklousky, C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2091. (j) Ley, S. V.; Norman, J.; Pinel, C. Ibid. 1994, 35, 2095. (k) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77. (1) Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835. Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
43. Synthetic approaches to 1: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643. (b) Eshelman, J. E.; Epps, J. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 749. Sin, N.; Kallmerten, J. Ibid. 1993, 34, 753. (d) Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (e) Rao, A. V. R.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111. (f) Ny, S.; Kallmerten, J. Ibid. 1993, 34, 753. (g) Pattenden, G.; Tankard, M.; Cherry, P. C. Ibid. 1993, 34, 2677. (h) Anderson, J. C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2087. Kouklousky, C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2091. (j) Ley, S. V.; Norman, J.; Pinel, C. Ibid. 1994, 35, 2095. (k) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77. (1) Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835. Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
44. Synthetic approaches to 1: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643. (b) Eshelman, J. E.; Epps, J. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 749. Sin, N.; Kallmerten, J. Ibid. 1993, 34, 753. Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (e) Rao, A. V. R.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111. (f) Ny, S.; Kallmerten, J. Ibid. 1993, 34, 753. (g) Pattenden, G.; Tankard, M.; Cherry, P. C. Ibid. 1993, 34, 2677. (h) Anderson, J. C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2087. Kouklousky, C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2091. (j) Ley, S. V.; Norman, J.; Pinel, C. Ibid. 1994, 35, 2095. (k) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77. (1) Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835. Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
45. Synthetic approaches to 1: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643. (b) Eshelman, J. E.; Epps, J. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 749. Sin, N.; Kallmerten, J. Ibid. 1993, 34, 753. Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (e) Rao, A. V. R.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111. (f) Ny, S.; Kallmerten, J. Ibid. 1993, 34, 753. (g) Pattenden, G.; Tankard, M.; Cherry, P. C. Ibid. 1993, 34, 2677. (h) Anderson, J. C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2087. Kouklousky, C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2091. (j) Ley, S. V.; Norman, J.; Pinel, C. Ibid. 1994, 35, 2095. (k) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77. (1) Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835. Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
46. Synthetic approaches to 1: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643. (b) Eshelman, J. E.; Epps, J. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 749. Sin, N.; Kallmerten, J. Ibid. 1993, 34, 753. Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (e) Rao, A. V. R.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111. (f) Ny, S.; Kallmerten, J. Ibid. 1993, 34, 753. (g) Pattenden, G.; Tankard, M.; Cherry, P. C. Ibid. 1993, 34, 2677. (h) Anderson, J. C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2087. Kouklousky, C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2091. (j) Ley, S. V.; Norman, J.; Pinel, C. Ibid. 1994, 35, 2095. (k) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77. (1) Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835. Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
47. Synthetic approaches to 1: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643. (b) Eshelman, J. E.; Epps, J. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 749. Sin, N.; Kallmerten, J. Ibid. 1993, 34, 753. Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (e) Rao, A. V. R.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111. (f) Ny, S.; Kallmerten, J. Ibid. 1993, 34, 753. (g) Pattenden, G.; Tankard, M.; Cherry, P. C. Ibid. 1993, 34, 2677. (h) Anderson, J. C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2087. Kouklousky, C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2091. (j) Ley, S. V.; Norman, J.; Pinel, C. Ibid. 1994, 35, 2095. (k) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77. (1) Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835. Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
48. Synthetic approaches to 1: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643. (b) Eshelman, J. E.; Epps, J. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 749. Sin, N.; Kallmerten, J. Ibid. 1993, 34, 753. Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (e) Rao, A. V. R.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111. (f) Ny, S.; Kallmerten, J. Ibid. 1993, 34, 753. (g) Pattenden, G.; Tankard, M.; Cherry, P. C. Ibid. 1993, 34, 2677. (h) Anderson, J. C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2087. (i) Kouklousky, C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2091. (j) Ley, S. V.; Norman, J.; Pinel, C. Ibid. 1994, 35, 2095. (k) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77. (1) Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835. Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
49. Synthetic approaches to 1: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643. (b) Eshelman, J. E.; Epps, J. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 749. Sin, N.; Kallmerten, J. Ibid. 1993, 34, 753. Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (e) Rao, A. V. R.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111. (f) Ny, S.; Kallmerten, J. Ibid. 1993, 34, 753. (g) Pattenden, G.; Tankard, M.; Cherry, P. C. Ibid. 1993, 34, 2677. (h) Anderson, J. C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2087. Kouklousky, C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2091. (j) Ley, S. V.; Norman, J.; Pinel, C. Ibid. 1994, 35, 2095. (k) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77. (1) Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835. Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
50. Synthetic approaches to 1: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643. (b) Eshelman, J. E.; Epps, J. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 749. Sin, N.; Kallmerten, J. Ibid. 1993, 34, 753. Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (e) Rao, A. V. R.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111. (f) Ny, S.; Kallmerten, J. Ibid. 1993, 34, 753. (g) Pattenden, G.; Tankard, M.; Cherry, P. C. Ibid. 1993, 34, 2677. (h) Anderson, J. C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2087. Kouklousky, C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2091. (j) Ley, S. V.; Norman, J.; Pinel, C. Ibid. 1994, 35, 2095. (k) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77. (1) Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835. Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
51. Synthetic approaches to 1: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643. (b) Eshelman, J. E.; Epps, J. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 749. Sin, N.; Kallmerten, J. Ibid. 1993, 34, 753. Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (e) Rao, A. V. R.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111. (f) Ny, S.; Kallmerten, J. Ibid. 1993, 34, 753. (g) Pattenden, G.; Tankard, M.; Cherry, P. C. Ibid. 1993, 34, 2677. (h) Anderson, J. C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2087. Kouklousky, C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2091. (j) Ley, S. V.; Norman, J.; Pinel, C. Ibid. 1994, 35, 2095. (k) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77. (1) Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835. Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
52. Synthetic approaches to 1: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643. (b) Eshelman, J. E.; Epps, J. L.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 749. Sin, N.; Kallmerten, J. Ibid. 1993, 34, 753. Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182. (e) Rao, A. V. R.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111. (f) Ny, S.; Kallmerten, J. Ibid. 1993, 34, 753. (g) Pattenden, G.; Tankard, M.; Cherry, P. C. Ibid. 1993, 34, 2677. (h) Anderson, J. C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2087. Kouklousky, C.; Ley, S. V.; Marsden, S. P. Ibid. 1994, 35, 2091. (j) Ley, S. V.; Norman, J.; Pinel, C. Ibid. 1994, 35, 2095. (k) Norley, M. C.; Kocienski, P. J.; Faller, A. Synlett 1994, 77. (1) Ley, S. V.; Kouklovsky, C. Tetrahedron 1994, 50, 835. (m) Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
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133. The stereochemistry of (+)-77 was determined by conversion to (+)-69. (Equation Presented)
134. The stereochemistry of (+)-81 was elucidated by conversion to (+)-83, identical to an authentic sample prepared from (+)-67. (Equation Presented)
135. See ref 62 for a discussion of steric vs stereoelectronic effects in nucleophilic addition reactions of α-substituted aldehydes.
136. The stereochemistry of (+)-84 was determined by conversion to (+)-88, identical to a sample prepared from (+)-83. (Equation Presented)
137. Schmid, C. R.; Bryant, J. D. Org. Synth. 1993, 72, 6.
138. 69 was elucidated via conversion to (+)-95, identical to a sample prepared from (+)-86. (Equation Presented)
139. McCauley, J. A. Ph.D. Thesis, University of Pennsylvania, 1996.
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144. Minor amounts (ca. 5% total) of internal stannanes 110 and 111 were formed in the hydrostannylation reaction. (Equation Presented)
145. 13C. Optical rotations were measured with a Perkin-Elmer Model 241 polarimeter. High-resolution mass spectra were obtained at the University of Pennsylvania Mass Spectrometry Service Center with either a VG Micromass 70/70H or VG ZAB-E spectrometer. Microanalyses were performed by Robertson Laboratories, Madison, NJ. Single-crystal X-ray structure determinations were performed at the University of Pennsylvania with an Enraf Nonius CAD-4 automated diffractometer.