Collect. Czech. Chem. Commun. 2011, 76, 1579-1594
https://doi.org/10.1135/cccc2011039
Published online 2011-12-23 10:44:00

Enantioselective synthesis of a taxol C ring

Cong Maa, Stéphanie Schiltza and Joëlle Prunetb,*

a Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, DCSO, F91128 Palaiseau, France
b WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ, UK

References

1. Oberlies N. H., Kroll D. J.: J. Nat. Prod. 2004, 67, 129. <https://doi.org/10.1021/np030498t>
2a. Nicolaou K. C., Dai W.-M., Guy R. K.: Angew. Chem., Int. Ed. Engl. 1994, 33, 15. <https://doi.org/10.1002/anie.199400151>
2b. Kingston D. G. I.: Chem. Commun. 2001, 867. <https://doi.org/10.1039/b100070p>
2c. For the total syntheses, see: Nicolaou K. C., Yang Z., Liu J. J., Ueno H., Nantermet P. G., Guy R. K., Claiborne C. F., Renaud J., Couladouros E. A., Paulvannan, K., Sorensen E. J.: Nature 1994, 367, 630. <https://doi.org/10.1038/367630a0>
2d. Nicolaou K. C., Nantermet P. G., Ueno H., Guy R. K., Couladouros E. A., Sorensen E. J.: J. Am. Chem. Soc. 1995, 117, 624. <https://doi.org/10.1021/ja00107a006>
2e. Nicolaou K. C., Liu J. J., Yang Z., Ueno H., Sorensen E. J., Claiborne C. F., Guy R. K., Hwang C. K., Nakada M., Nantermet P. G.: J. Am. Chem. Soc. 1995, 117, 634. <https://doi.org/10.1021/ja00107a007>
2f. Nicolaou K. C., Yang Z., Liu J. J., Nantermet P. G., Claiborne C. F., Renaud, J., Guy R. K., Shibayama K.: J. Am. Chem. Soc. 1995, 117, 645. <https://doi.org/10.1021/ja00107a008>
2g. Nicolaou K. C., Ueno H., Liu J. J., Nantermet P. G., Yang Z., Renaud J., Paulvannan K., Chadha R.: J. Am. Chem. Soc. 1995, 117, 653. <https://doi.org/10.1021/ja00107a009>
2h. Holton R. A., Somoza C., Kim H. B., Liang F., Biediger R. J., Boatman P. D., Shindo M., Smith C. C., Kim S., Nadizadeh H., Suzuki Y., Tao C., Vu P., Tang S., Zhang P., Murthi K. K., Gentile L. N., Liu J. H.: J. Am. Chem. Soc. 1994, 116, 1597. <https://doi.org/10.1021/ja00083a066>
2i. Holton R. A., Kim H. B., Somoza C., Liang F., Biediger R. J., Boatman P. D., Shindo M., Smith C. C., Kim S., Nadizadeh H., Suzuki Y., Tao C., Vu P., Tang S., Zhang P., Murthi K. K., Gentile L. N., Liu J. H.: J. Am. Chem. Soc. 1994, 116, 1599. <https://doi.org/10.1021/ja00083a067>
2j. Masters J. J., Link J. T., Snyder L. B., Young W. B., Danishefsky S.: Angew. Chem., Int. Ed. Engl. 1995, 34, 1723. <https://doi.org/10.1002/anie.199517231>
2k. Wender P. A., Badham N. F., Conway S. P., Floreancig P. E., Glass T. E., Gränicher C., Houze J. B., Jänichen J., Lee D., Marquess D. G., McGrane P. L., Meng W., Mucciaro T. P., Mühlebach M., Natchus M. G., Paulsen H., Rawlins D. B., Satkofsky J., Shuker A. J., Sutton J. C., Taylor R. E., Tomooka K.: J. Am. Chem. Soc. 1997, 119, 2755. <https://doi.org/10.1021/ja9635387>
2l. Wender P. A., Badham N. F., Conway S. P., Floreancig P. E., Glass T. E., Houze J. B., Krauss N. E., Lee D., Marquess D. G., McGrane P. L., Meng W., Natchus M. G., Shuker A. J., Sutton J. C., Taylor R. E.: J. Am. Chem. Soc. 1997, 119, 2757. <https://doi.org/10.1021/ja963539z>
2m. Mukaiyama T., Shiina I., Iwadare H., Saitoh M., Nishimura T., Ohkawa N., Sakoh H., Nishimura H., Tani Y.-I., Hasegawa M., Yamada K., Saito K.: Chem. Eur. J. 1999, 5, 121. <https://doi.org/10.1002/(SICI)1521-3765(19990104)5:1<121::AID-CHEM121>3.0.CO;2-O>
2n. Morihara, K., Hara R., Kawahara S., Nishimori T., Nakamura N., Kusama H., Kuwajima I.: J. Am. Chem. Soc. 1998, 120, 12980. <https://doi.org/10.1021/ja9824932>
3. Doi T., Fuse S., Miyamoto S., Nakai K., Sasuga D., Takahashi T.: Chem. Asian J. 2006, 1, 370. <https://doi.org/10.1002/asia.200600156>
4. Swindell C. S., Patel B. P.: J. Org. Chem. 1990, 55, 3. <https://doi.org/10.1021/jo00288a002>
5a. Muller B., Delaloge F., den Hartog M., Férézou J.-P., Pancrazi A., Prunet J., Lallemand J. Y., Neuman A., Prangé T.: Tetrahedron Lett. 1996, 37, 3313. <https://doi.org/10.1016/0040-4039(96)00538-2>
5b. Delaloge F., Pancrazi A., Prunet J., Lallemand J.-Y.: Tetrahedron Lett. 1997, 38, 237. <https://doi.org/10.1016/S0040-4039(96)02306-4>
5c. Grimaud L., Férézou J.-P., Prunet J., Lallemand J.-Y.: Tetrahedron 1997, 53, 9253. <https://doi.org/10.1016/S0040-4020(97)00606-6>
5d. Muller B., Férézou J.-P., Lallemand J.-Y., Pancrazi A., Prunet J., Prangé T.: Tetrahedron Lett. 1998, 39, 279. <https://doi.org/10.1016/S0040-4039(97)10512-3>
5e. Bourgeois D., Lallemand J. Y., Pancrazi A., Prunet J.: Synlett 1999, 1555. <https://doi.org/10.1055/s-1999-2889>
5f. Bourgeois D., Pancrazi A., Ricard L., Prunet J.: Angew. Chem. Int. Ed. 2000, 39, 725. <https://doi.org/10.1002/(SICI)1521-3773(20000218)39:4<725::AID-ANIE725>3.0.CO;2-I>
5g. Bourgeois D., Mahuteau J., Pancrazi A., Nolan S. P., Prunet J.: Synthesis 2000, 869. <https://doi.org/10.1055/s-2000-6263>
5h. Bourgeois D., Prunet J., Pancrazi A., Prangé T., Lallemand J.-Y.: Eur. J. Org. Chem. 2000, 4029. <https://doi.org/10.1002/1099-0690(200012)2000:24<4029::AID-EJOC4029>3.0.CO;2-0>
5i. Bourgeois D., Pancrazi A., Nolan S. P., Prunet J.: J. Organomet. Chem. 2002, 643–644, 247. <https://doi.org/10.1016/S0022-328X(01)01269-4>
5j. Schiltz S., Ma C., Ricard L., Prunet J.: J. Organomet. Chem. 2006, 691, 5438. <https://doi.org/10.1016/j.jorganchem.2006.08.078>
5k. Ma C., Schiltz S., Le Goff X. F., Prunet J.: Chem. Eur. J. 2008, 14, 7314.
6a. Brown P. A., Jenkins P. R., Fawcett J., Russell D. R.: J. Chem. Soc., Chem. Commun. 1984, 253. <https://doi.org/10.1039/c39840000253>
6b. Bonnert R. V., Jenkins P. R.: J. Chem. Soc., Chem. Commun. 1987, 1540. <https://doi.org/10.1039/c39870001540>
6c. Brown P. A., Jenkins P. R.: J. Chem. Soc., Perkin Trans. 1 1986, 1303. <https://doi.org/10.1039/p19860001303>
6d. Bonnert R. V., Jenkins P. R.: J. Chem. Soc., Perkin Trans. 1 1989, 413. <https://doi.org/10.1039/p19890000413>
6e. Rubenstein S. M., Williams R. M.: J. Org. Chem. 1995, 60, 6215. <https://doi.org/10.1021/jo00127a029>
7a. Wieland P., Miescher K.: Helv. Chim. Acta 1950, 33, 2215. <https://doi.org/10.1002/hlca.19500330730>
7b. Gutzwiller J., Buchschacher P., Fürst A.: Synthesis 1977, 167. <https://doi.org/10.1055/s-1977-24303>
7c. Buchschacher P., Fürst A., Gutzwiller J.: Org. Synth. 1985, 63, 37.
8. Toda F., Kiyoshige K., Yagi M.: Angew. Chem., Int. Ed. Engl. 1989, 28, 320. <https://doi.org/10.1002/anie.198903201>
9. Yang D., Zhang C.: J. Org. Chem. 2001, 66, 4814. <https://doi.org/10.1021/jo010122p>
10. Labadie G. R., Luna L. E., Gonzalez-Sierra M., Cravero R. M.: Eur. J. Org. Chem. 2003, 3429. <https://doi.org/10.1002/ejoc.200300202>
11. Frigerio M., Santagostino M., Sputore S.: J. Org. Chem. 1999, 64, 4537. <https://doi.org/10.1021/jo9824596>
12. Smith III A. B., Doughty V. A., Sfouggatakis C., Bennett C. S., Koyanagi J., Takeuchi M.: Org. Lett. 2002, 4, 783. <https://doi.org/10.1021/ol017273z>
13. We chose to protect the hemiacetal as a trityl acetal because of the mild conditions required for this transformation.
14. Paquette L. A., Sturino C. F., Wang X., Prodger J. C., Koh D.: J. Am. Chem. Soc. 1996, 118, 5620. <https://doi.org/10.1021/ja960334h>
15. Felpin F.-X., Bertrand M.-J., Lebreton J.: Tetrahedron 2002, 58, 7381. <https://doi.org/10.1016/S0040-4020(02)00819-0>