Rhodium-carbenoid-mediated intermolecular O-H insertion reactions: A dramatic additive effect. Application in the synthesis of an ascomycin derivative

Tetrahedron Letters

Volumn 41, Issue 12, 2000, Pages 1877-1881

  Nelson, Todd D ^a   Song, Zhiguo Jake ^a   Thompson, Andrew S ^a   Zhao, Mangzhu ^a   Demarco, Anthony ^a   Reamer, Robert A ^a   Huntington, Martha F ^a   Grabowski, Edward J J ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASCOMYCIN DERIVATIVE; CARBENOID; MACROLIDE; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; REACTION ANALYSIS; SYNTHESIS;

EID: 0034681747     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00069-1     Document Type: Article

References (21)

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3. Byrne, K. M.; Shafiee, A.; Nielsen, J. B.; Arison, B.; Monaghan, R. L.; Kaplan, L. In Microbial Metabolites; Nash, C.; Hunter-Cevera, J.; Cooper, R.; Eveleigh, D. E.; Hamill, R., Eds.; Wm. C. Brown Publishers, 1992; Vol. 32, p. 29.
4. (a) Burk, R. M.; Gac, T. S.; Roof, M. B. Tetrahedron Lett. 1994, 35, 8111;
5. (b) Wagner, R.; Rhoades, T. A.; Or, Y. S.; Lane, B. C.; Hsieh, G.; Mollison, K. W.; Luly, J. R. J. Med. Chem. 1998, 41, 1764.
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7. (a) Hauptmann, S.; Wilde, H. J. Prakt. Chem. 1969, 604;
8. (b) Pellcciari, R.; Curini, M.; Spagnoli, N.; Arch. Pharm. 1984, 317, 38.
9. (a) For a review on O-H insertion of carbenoids, see: Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10 811;
10. (b) for other examples of carbenoid O-H insertion reactions, see: Noels, A. F.; Demonceau, N.; Petiniot, N.; Hubert, A. J.; Teyssié, P. Tetrahedron 1982, 38, 2733; Haigh, D. Tetrahedron 1994, 50, 3177; Cox, G. G., Miller, D. J.; Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195;
11. (b) for other examples of carbenoid O-H insertion reactions, see: Noels, A. F.; Demonceau, N.; Petiniot, N.; Hubert, A. J.; Teyssié, P. Tetrahedron 1982, 38, 2733; Haigh, D. Tetrahedron 1994, 50, 3177; Cox, G. G., Miller, D. J.; Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195;
12. (b) for other examples of carbenoid O-H insertion reactions, see: Noels, A. F.; Demonceau, N.; Petiniot, N.; Hubert, A. J.; Teyssié, P. Tetrahedron 1982, 38, 2733; Haigh, D. Tetrahedron 1994, 50, 3177; Cox, G. G., Miller, D. J.; Moody, C. J.; Sie, E.-R. H. B.; Kulagowski, J. J. Tetrahedron 1994, 50, 3195;
13. (c) for leading references on ligand effects in rhodium carbenoid reactions, see: Padwa, A.; Austin, D. J.; Hornbuckle, S. F. J. Org. Chem. 1995, 61, 63; Doyle, M. P.; Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968;
14. (c) for leading references on ligand effects in rhodium carbenoid reactions, see: Padwa, A.; Austin, D. J.; Hornbuckle, S. F. J. Org. Chem. 1995, 61, 63; Doyle, M. P.; Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968;
15. 2H insertion of carbenoids, see: Shinada, T.; Kawakami, T.; Sakai, H.; Takada, I.; Ohfune, Y. Tetrahedron Lett. 1998, 39, 3757.
16. 3OD), 183.5, 43.0, 39.2, 36.4, 28.0.
17. 3CN) δ 212.8, 198.6, 197.9, 170.4, 166.5, 139.4, 136.5, 133.8, 133.5, 132.9, 132.3, 130.7, 130.5, 129.6, 129.3, 128.7, 127.9, 124.7, 124.6, 98.2, 84.3, 83.5, 79.7, 76.2, 74.7, 74.5, 73.9, 70.4, 57.5 (2 C), 57.2, 56.9, 55.8, 49.6, 46.1, 41.0, 39.9, 36.9, 35.5, 35.4, 34.1, 33.4, 31.5, 31.1, 28.5, 27.2, 25.5, 25.1, 21.9, 20.3, 16.5, 16.1, 13.7, 12.0, 10.1.
18. This protection was necessary so the competing reduction of C22 ketone is minimized.
19. 3 triethylamine complex: Cai, D.; Tschaen, D.; Shi, Y.-J.; Verhoeven, T. R.; Reamer, R. A.; Douglas, A. W. Tetrahedron Lett. 1993, 34, 3243.
20. R/S ratios were determined by HPLC on a YMC PVA-sil column 96:4 (hex:EtOH); 1.5 mL/min; 215 nm. NMR data for macrocycle 1 matched the authentic sample. The (R) isomer was also provided by F. Wong (Merck).
21. 3CN) δ 212.8, 198.6, 170.4, 166.5, 140.1, 139.4, 134.3, 133.9, 132.9, 132.3, 128.8, 128.6, 128.5, 127.1, 126.7, 125.8, 125.6, 124.7, 98.2, 84.6, 83.8, 79.7, 77.4, 76.2, 74.6, 74.5, 73.9, 70.4, 57.5 (2 C), 57.3, 56.7, 55.8, 49.6, 46.1, 41.0, 39.9, 36.8, 35.5, 35.3, 34.1, 33.4, 31.4, 31.2, 28.5, 27.2, 25.5, 25.1, 22.0, 20.3, 16.5, 16.1, 13.7, 12.0, 10.1.