Stereocontrolled total synthesis of potent immunosuppressant FR901483

Organic Letters

Volumn 6, Issue 16, 2004, Pages 2729-2731

  Kan, Toshiyuki ^a   Fujimoto, Teppei ^a   Ieda, Shigeru ^a   Asoh, Yusuke ^a   Kitaoka, Haruka ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FR 901483; IMMUNOSUPPRESSIVE AGENT; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; DRUG POTENCY; DRUG SYNTHESIS; IMMUNOSUPPRESSIVE TREATMENT; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ALDEHYDES; ALKYLATION; ASCOMYCOTA; IMMUNOSUPPRESSIVE AGENTS; METHYLAMINES; ORGANOPHOSPHORUS COMPOUNDS;

EID: 4344580504     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049074w     Document Type: Article

References (22)

1. Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara, M. J. Antibiot. 1996, 49, 37.
2. For a review of biomimetic synthesis of this family compounds, see: Takayama, H. J. Synth. Org. Chem. Jpn. 2002, 60, 350.
3. For the synthetic studies, see: (a) Fujimoto, T.; Kitaoka, H.; Ieda, S.; Kan, T.; Fukuyama, T. Abstract of papers, 79th Symposium on Organic Synthesis, Japan; The Society of Synthetic Organic Chemistry, Japan: Tokyo, June 2001; p 17. (b) Suzuki, H.; Yamazaki, N.; Kibayashi, C. Tetrahedron Lett. 2001, 42, 3013. Brummond, K. M.; Lu, J. L. Org. Lett. 2001, 3, 1347. Wardrop, D. J.; Zhang, W. M. Org. Lett. 2001, 3, 2001. (e) Puigbo, G.; Diaba, F.; Bonjoch, J. Tetrahedron 2003, 59, 2657. (f) Bonjoch, J.; Diaba, F.; Puigbo, G.; Peidro, E.; Sole, D. Tetrahedron Lett. 2003, 44, 8387.
4. For the synthetic studies, see: (a) Fujimoto, T.; Kitaoka, H.; Ieda, S.; Kan, T.; Fukuyama, T. Abstract of papers, 79th Symposium on Organic Synthesis, Japan; The Society of Synthetic Organic Chemistry, Japan: Tokyo, June 2001; p 17. (b) Suzuki, H.; Yamazaki, N.; Kibayashi, C. Tetrahedron Lett. 2001, 42, 3013. Brummond, K. M.; Lu, J. L. Org. Lett. 2001, 3, 1347. Wardrop, D. J.; Zhang, W. M. Org. Lett. 2001, 3, 2001. (e) Puigbo, G.; Diaba, F.; Bonjoch, J. Tetrahedron 2003, 59, 2657. (f) Bonjoch, J.; Diaba, F.; Puigbo, G.; Peidro, E.; Sole, D. Tetrahedron Lett. 2003, 44, 8387.
5. For the synthetic studies, see: (a) Fujimoto, T.; Kitaoka, H.; Ieda, S.; Kan, T.; Fukuyama, T. Abstract of papers, 79th Symposium on Organic Synthesis, Japan; The Society of Synthetic Organic Chemistry, Japan: Tokyo, June 2001; p 17. (b) Suzuki, H.; Yamazaki, N.; Kibayashi, C. Tetrahedron Lett. 2001, 42, 3013. (c) Brummond, K. M.; Lu, J. L. Org. Lett. 2001, 3, 1347. Wardrop, D. J.; Zhang, W. M. Org. Lett. 2001, 3, 2001. (e) Puigbo, G.; Diaba, F.; Bonjoch, J. Tetrahedron 2003, 59, 2657. (f) Bonjoch, J.; Diaba, F.; Puigbo, G.; Peidro, E.; Sole, D. Tetrahedron Lett. 2003, 44, 8387.
6. For the synthetic studies, see: (a) Fujimoto, T.; Kitaoka, H.; Ieda, S.; Kan, T.; Fukuyama, T. Abstract of papers, 79th Symposium on Organic Synthesis, Japan; The Society of Synthetic Organic Chemistry, Japan: Tokyo, June 2001; p 17. (b) Suzuki, H.; Yamazaki, N.; Kibayashi, C. Tetrahedron Lett. 2001, 42, 3013. (c) Brummond, K. M.; Lu, J. L. Org. Lett. 2001, 3, 1347. (d) Wardrop, D. J.; Zhang, W. M. Org. Lett. 2001, 3, 2001. (e) Puigbo, G.; Diaba, F.; Bonjoch, J. Tetrahedron 2003, 59, 2657. (f) Bonjoch, J.; Diaba, F.; Puigbo, G.; Peidro, E.; Sole, D. Tetrahedron Lett. 2003, 44, 8387.
7. For the synthetic studies, see: (a) Fujimoto, T.; Kitaoka, H.; Ieda, S.; Kan, T.; Fukuyama, T. Abstract of papers, 79th Symposium on Organic Synthesis, Japan; The Society of Synthetic Organic Chemistry, Japan: Tokyo, June 2001; p 17. (b) Suzuki, H.; Yamazaki, N.; Kibayashi, C. Tetrahedron Lett. 2001, 42, 3013. (c) Brummond, K. M.; Lu, J. L. Org. Lett. 2001, 3, 1347. (d) Wardrop, D. J.; Zhang, W. M. Org. Lett. 2001, 3, 2001. (e) Puigbo, G.; Diaba, F.; Bonjoch, J. Tetrahedron 2003, 59, 2657. (f) Bonjoch, J.; Diaba, F.; Puigbo, G.; Peidro, E.; Sole, D. Tetrahedron Lett. 2003, 44, 8387.
8. For the synthetic studies, see: (a) Fujimoto, T.; Kitaoka, H.; Ieda, S.; Kan, T.; Fukuyama, T. Abstract of papers, 79th Symposium on Organic Synthesis, Japan; The Society of Synthetic Organic Chemistry, Japan: Tokyo, June 2001; p 17. (b) Suzuki, H.; Yamazaki, N.; Kibayashi, C. Tetrahedron Lett. 2001, 42, 3013. (c) Brummond, K. M.; Lu, J. L. Org. Lett. 2001, 3, 1347. (d) Wardrop, D. J.; Zhang, W. M. Org. Lett. 2001, 3, 2001. (e) Puigbo, G.; Diaba, F.; Bonjoch, J. Tetrahedron 2003, 59, 2657. (f) Bonjoch, J.; Diaba, F.; Puigbo, G.; Peidro, E.; Sole, D. Tetrahedron Lett. 2003, 44, 8387.
9. For total syntheses, see: (a) Snider, B. B.; Lin, H. J. Am. Chem. Soc. 1999, 121, 7778. (b) Scheffler, G.; Seike, H.; Sorensen, E. J. Angew. Chem., Int. Ed. 2000, 39, 4593. Ousmer, M.; Braun, N. A.; Bavoux, C.; Perrin, M.; Ciufolini, M. A. J. Am. Chem. Soc. 2001, 123, 7543. Maeng, J.; Funk, R. L. Org. Lett. 2001, 3, 1125.
10. For total syntheses, see: (a) Snider, B. B.; Lin, H. J. Am. Chem. Soc. 1999, 121, 7778. (b) Scheffler, G.; Seike, H.; Sorensen, E. J. Angew. Chem., Int. Ed. 2000, 39, 4593. Ousmer, M.; Braun, N. A.; Bavoux, C.; Perrin, M.; Ciufolini, M. A. J. Am. Chem. Soc. 2001, 123, 7543. Maeng, J.; Funk, R. L. Org. Lett. 2001, 3, 1125.
11. For total syntheses, see: (a) Snider, B. B.; Lin, H. J. Am. Chem. Soc. 1999, 121, 7778. (b) Scheffler, G.; Seike, H.; Sorensen, E. J. Angew. Chem., Int. Ed. 2000, 39, 4593. (c) Ousmer, M.; Braun, N. A.; Bavoux, C.; Perrin, M.; Ciufolini, M. A. J. Am. Chem. Soc. 2001, 123, 7543. Maeng, J.; Funk, R. L. Org. Lett. 2001, 3, 1125.
12. For total syntheses, see: (a) Snider, B. B.; Lin, H. J. Am. Chem. Soc. 1999, 121, 7778. (b) Scheffler, G.; Seike, H.; Sorensen, E. J. Angew. Chem., Int. Ed. 2000, 39, 4593. (c) Ousmer, M.; Braun, N. A.; Bavoux, C.; Perrin, M.; Ciufolini, M. A. J. Am. Chem. Soc. 2001, 123, 7543. (d) Maeng, J.; Funk, R. L. Org. Lett. 2001, 3, 1125.
13. For a review on enantioselective desymmetrization, see: Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 13, 1765.
14. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
15. For a similar reaction, see ref 4d.
16. 3 reduction and selective deprotection of the TBS ether has already been reported in ref 4d. However, the transformation of 8 to 10 has been developed independently in our laboratory; see ref 3a.
17. Since the alkylation of 10 without TMEDA provided concomitantly the dialkylated product, TMEDA presumably plays a key role in this reaction. Similar enhancement of the mono-alkylation reaction by the addition of alkylamine derivatives was reported; see: Goto, M.; Akimoto, K.; Aoki, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1999, 40, 8129.
18. 2, see: (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (b) Molander, G. A. Chem. Rev. 1992, 92, 29.
19. 2, see: (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (b) Molander, G. A. Chem. Rev. 1992, 92, 29.
20. 2 by addition of HMPA has been reported; see: Inanaga, J.; Yamaguchi, M. J. Synth. Org. Chem. Jpn. 1989, 47, 200.
21. For a review of the phosphoramidite method, see: Iyer, R. P. Tetrahedron 1992, 48, 2223.
22. For a similar regioselective phosphitylation, see ref 4a.