Collect. Czech. Chem. Commun. 2000, 65, 490-510
https://doi.org/10.1135/cccc20000490

Studies Toward an Asymmetric Synthesis of CP-263,114 and CP-225,917

Jean-François Devaux, Steven V. O'Neil, Nathalie Guillo and Leo A. Paquette*

Evans Chemical Laboratories, The Ohio State University, Columbus, OH 43210, U.S.A

References

1a. Dabrah T. T., Harwood H. J., Huang L. H., Jankovich N. D., Kaneko T., Li J.-C., Lindsey S., Moshier P. M., Subashi T. A., Therrien M., Watts P. C.: J. Antibiot. 1997, 50, 1. <https://doi.org/10.7164/antibiotics.50.1>
1b. Dabrah T. T., Kaneko T., Massefski W., Jr., Whipple E. B.: J. Am. Chem. Soc. 1997, 119, 1594. <https://doi.org/10.1021/ja961000v>
2a. Leonard D. M.: J. Med. Chem. 1997, 40, 2971. <https://doi.org/10.1021/jm970226l>
2b. Buss J. E., Morsters J. C.: Chem. Biol. 1995, 2, 787. <https://doi.org/10.1016/1074-5521(95)90083-7>
2c. Goldstein J. L., Brown M. S.: Nature 1990, 343, 425. <https://doi.org/10.1038/343425a0>
3a. Watson N. S., Procopiou P. A.: Prog. Med. Chem. 1996, 33, 331. <https://doi.org/10.1016/S0079-6468(08)70308-4>
3b. Biller S. A., Neuenschwander K., Pompipom M. M., Poulter C. D.: Curr. Pharm. Design 1996, 2, 1.
4a. Davies H. M. L., Calvo R., Ahmed G.: Tetrahedron Lett. 1997, 38, 1737. <https://doi.org/10.1016/S0040-4039(97)00204-9>
4b. Nicolaou K. C., Härter M. W., Boulton L., Jandeleit B.: Angew. Chem., Int. Ed. Engl. 1997, 36, 1194. <https://doi.org/10.1002/anie.199711941>
4c. Nicolaou K. C., Postema M. H. D., Miller N. D., Yang G.: Angew. Chem., Int. Ed. Engl. 1997, 36, 2821. <https://doi.org/10.1002/anie.199728211>
4d. Sgarbi P. W. M., Clive D. L. J.: J. Chem. Soc., Chem. Commun. 1997, 2157. <https://doi.org/10.1039/a706075k>
4e. Armstrong A., Critchley T. J., Mortlook A. A.: Synlett 1998, 552. <https://doi.org/10.1055/s-1998-1699>
4f. Kwon O., Su D.-S., Meng D., Deng W., D’Amico D. C., Danishefsky S. J.: Angew. Chem., Int. Ed. Engl. 1998, 37, 1877. <https://doi.org/10.1002/(SICI)1521-3773(19980803)37:13/14<1877::AID-ANIE1877>3.0.CO;2-2>
4g. Kwon O., Su D.-S., Meng D., Deng W., D’Amico D. C., Danishefsky S. J.: Angew. Chem., Int. Ed. Engl. 1998, 37, 1880. <https://doi.org/10.1002/(SICI)1521-3773(19980803)37:13/14<1880::AID-ANIE1880>3.0.CO;2-5>
4h. Waizumi N., Itoh T., Fukuyama T.: Tetrahedron Lett. 1998, 39, 6015. <https://doi.org/10.1016/S0040-4039(98)01236-2>
4i. Chen C., Layton M. E., Shair M. D.: J. Am. Chem. Soc. 1998, 120, 10784. <https://doi.org/10.1021/ja982581m>
4j. Bio M. M., Leighton J. L.: J. Am. Chem. Soc. 1999, 121, 890. <https://doi.org/10.1021/ja983609x>
4k. Nicolaou K. C., He Y., Fong K. C., Yoon W. H., Choi H.-S., Zhong Y.-L., Baran P. S.: Org. Lett. 1999, 1, 63. <https://doi.org/10.1021/ol990551y>
4l. Nicolaou K. C., Baran P. S., Jautelat R., He Y., Fong K. C., Choi H.-S., Yoon W. H., Zhong Y.-L.: Angew. Chem., Int. Ed. Engl. 1999, 38, 549. <https://doi.org/10.1002/(SICI)1521-3773(19990215)38:4<549::AID-ANIE549>3.0.CO;2-O>
4m. Meng D., Danishefsky S. J.: Angew. Chem., Int. Ed. Engl. 1999, 38, 1485. <https://doi.org/10.1002/(SICI)1521-3773(19990517)38:10<1485::AID-ANIE1485>3.0.CO;2-1>
4n. Clive D. L. J., Sun S., He X., Zhang J., Gagiardini V.: Tetrahedron Lett. 1999, 40, 4605. <https://doi.org/10.1016/S0040-4039(99)00743-1>
4o. Yoshimitzu T., Yanagiya M., Nagaoka H.: Tetrahedron Lett. 1999, 40, 5215. <https://doi.org/10.1016/S0040-4039(99)00941-7>
5a. Nicolaou K. C., Baran P. S., Zhong Y.-L., Choi H.-S., Yoon W. H., He Y., Fong K. C.: Angew. Chem., Int. Ed. Engl. 1999, 38, 1669. <https://doi.org/10.1002/(SICI)1521-3773(19990601)38:11<1669::AID-ANIE1669>3.0.CO;2-D>
5b. Nicolaou K. C., Baran P. S., Zhong Y.-L., Fong K. C., He Y., Yoon W. H., Choi H.-S.: Angew. Chem., Int. Ed. Engl. 1999, 38, 1676. <https://doi.org/10.1002/(SICI)1521-3773(19990601)38:11<1676::AID-ANIE1676>3.0.CO;2-T>
6a. Stinson S.: Chem. Eng. News 1995, May 22, 29. <https://doi.org/10.1021/cen-v073n021.p029>
6b. Consult also Meng D., Tan Q., Danishefsky S. J.: Angew. Chem., Int. Ed. Engl. 1999, 38, 3197. <https://doi.org/10.1002/(SICI)1521-3773(19991102)38:21<3197::AID-ANIE3197>3.0.CO;2-6>
7. Paquette L. A., Bzowej E. I., Branan B. M., Stanton K. J.: J. Org. Chem. 1995, 60, 7277. <https://doi.org/10.1021/jo00127a037>
8. Corey E. J., Katzenellenbogen J. A., Roman S. A., Gilman N. W.: Tetrahedron Lett. 1971, 1821. <https://doi.org/10.1016/S0040-4039(01)87471-2>
9. Jones T. K., Denmark S. E.: Org. Synth. 1985, 64, 182.
10. Schmidt S. P., Brooks D. W.: Tetrahedron Lett. 1987, 28, 767. <https://doi.org/10.1016/S0040-4039(01)80984-9>
11a. Vanhessche K. P. M., Wang Z. M., Sharpless K. B.: Tetrahedron Lett. 1994, 35, 3469. <https://doi.org/10.1016/S0040-4039(00)73212-6>
11b. Kolb H. C., VanNieuwenhze M. S., Sharpless K. B.: Chem. Rev. 1994, 94, 2483. <https://doi.org/10.1021/cr00032a009>
12. Mori K., Abe K.: Liebigs Ann. Chem. 1995, 943. <https://doi.org/10.1002/jlac.1995199506135>
13a. Dale J. A., Dull D. L., Mosher H. S.: J. Org. Chem. 1969, 34, 2543. <https://doi.org/10.1021/jo01261a013>
13b. Dale J. A., Mosher H. S.: J. Am. Chem. Soc. 1973, 95, 512. <https://doi.org/10.1021/ja00783a034>
13c. Ward D. E., Rhee C. K.: Tetrahedron Lett. 1991, 32, 7165. <https://doi.org/10.1016/0040-4039(91)80466-J>
14. Abrams S. R., Shaw A. C.: Org. Synth. 1987, 66, 127.
15. De Medeiros E. F., Herbert J. M., Taylor R. J. K.: J. Chem. Soc., Perkin Trans. 1 1991, 2725. <https://doi.org/10.1039/p19910002725>
16a. Van Bekkum H., Van den Bosch C. B., Van Minnen-Pathuis G., De Mos J. C., Van Wijk A. M.: Rec. Trav. Chim. Pays-Bas 1971, 90, 137. <https://doi.org/10.1002/recl.19710900203>
16b. Beckwith A. L. J., Roberts D. H.: J. Am. Chem. Soc. 1986, 108, 5893. <https://doi.org/10.1021/ja00279a039>
17. Schultz A. G., Taveras A. G., Harrington R. E.: Tetrahedron Lett. 1988, 29, 3907. <https://doi.org/10.1016/S0040-4039(00)80377-9>
18a. Bailey W. F., Puzalan E. R.: J. Org. Chem. 1990, 55, 5404. <https://doi.org/10.1021/jo00306a021>
18b. Negishi E., Swanson D. R., Rousset C. J.: J. Org. Chem. 1990, 55, 5406. <https://doi.org/10.1021/jo00306a022>
19. Krapcho A. P.: Synthesis 1982, 805, 893. <https://doi.org/10.1055/s-1982-29991>
20. Liotta D., Sunay U., Santiesteban H., Markiewicz W.: J. Org. Chem. 1981, 46, 2605. <https://doi.org/10.1021/jo00326a001>
21. Gassman P. G., Schenk W. N.: J. Org. Chem. 1977, 42, 918. <https://doi.org/10.1021/jo00425a040>
22. Kinney W. A., Crouse G. D., Paquette L. A.: J. Org. Chem. 1983, 48, 4986. <https://doi.org/10.1021/jo00173a040>
23. Luche J. L.: J. Chem. Soc., Chem. Commun. 1978, 601. <https://doi.org/10.1039/c39780000601>
24. Paquette L. A., Wang T.-Z., Philippo C. M. G., Wang S.: J. Am. Chem. Soc. 1994, 116, 3367. <https://doi.org/10.1021/ja00087a023>
25. Trost B. M., Fray M. J.: Tetrahedron Lett. 1988, 29, 2163. <https://doi.org/10.1016/S0040-4039(00)86699-X>
26. Prepared from the known ethyl ester: Petter R. C., Banerjee S., Englard S.: J. Org. Chem. 1990, 55, 3088. <https://doi.org/10.1021/jo00297a025>
27. Review: Paquette L. A., O’Neil S. V., Guillo N., Zeng Q., Young D. G.: Synlett 1999, 1857. <https://doi.org/10.1055/s-1999-2959>
28. Hanessian S., Sakito Y., Dhanoa D., Baptistella L.: Tetrahedron 1989, 45, 6623. <https://doi.org/10.1016/S0040-4020(01)89132-8>
29. Olsen R. K., Feng X.: Tetrahedron Lett. 1991, 32, 5721. <https://doi.org/10.1016/S0040-4039(00)93539-1>
30. Paterson I., Tillyer R. D.: J. Org. Chem. 1993, 58, 4182. <https://doi.org/10.1021/jo00068a002>
31. Skotnicki J. S., Kearney R. M., Smith A. L.: Tetrahedron Lett. 1994, 35, 197. <https://doi.org/10.1016/S0040-4039(00)76509-9>
32. Paterson I., Nowak T.: Tetrahedron Lett. 1996, 37, 8243. <https://doi.org/10.1016/0040-4039(96)01879-5>
33. The Kakisawa method is based on the adoption of an idealized conformation in which the carbinyl proton, ester carbonyl, and trifluoromethyl groups of the MTPA ester are in the same plane: Ohtani I., Kusumi T., Kashman Y., Kakisawa H.: J. Am. Chem. Soc. 1991, 113, 4092. <https://doi.org/10.1021/ja00011a006>