Stereoselective Synthesis of γ,δ-Epoxy-β-methyl-γ-(trimethylsilyl)alkanols. Synthesis of the C(1)-C(7) Segment of 6-Deoxyerythronolide B

Journal of the American Chemical Society

Volumn 107, Issue 19, 1985, Pages 5541-5543

  Kobayashi, Yuichi ^a   Uchivama, Hiroshi ^a   Kanbara, Hiroshi ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001619975     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00305a045     Document Type: Article

References (11)

1. (a) Sato, F.; Kusakabe, M.; Kobayashi, Y. J. Chem. Soc., Chem. Commun. 1984, 1130. (b) Kobayashi, Y.; Kitano, Y.; Sato, F. J. Chem. Soc., Chem. Commun. 1984, 1329. (c) Sato, F.; Kusakabe, M.; Kato, T.; Kobayashi, Y. J. Chem. Soc., Chem. Commun. 1984, 1331.
2. For reviews, see: Sharpless, K. B.; Verhoeven, T. R. Aldrichimica Acta 1979, 12, 63. Bartlett, P. A. Tetrahedron 1980, 36, 2. Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Aldrichimica Acta. 1983, 39, 2323.
3. Stereoselective epoxidation of acyclic homoallyl alcohols, see: Mihelich, E. D.; Daniels, K.; Eickhoff, D. J. J. Am. Chem. Soc. 1981, 103, 7690. Schmid, G.; Fukuyama, T.; Akasaka, K.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 259. Johnson, M. R.; Kishi, Y. Tetrahedron Lett. 1979, 4347. Williams, D. R.; Grote, J.; Harigaya, Y. J. Am. Chem. Soc. 1984, 25, 5231. Other examples of epoxidation of homoallyl alcohols, see: Yamamoto, Y.; Yatagai, H.; Maruyama, K. J. Am. Chem. Soc. 1981, 103, 3229. Beau, J.-M,; Aburaki, S.; Pougny, J.-R.; Sinäy, P. J. Am. Chem. Soc. 1983, 105, 621. Kozikowski, A. P.; Schmiesing, R. J.; Sorgi, K. L. Tetrahedron Lett. 1981, 22, 2059. Hiyama, T.; Kimura, K.; Nozaki, H. J. Am. Chem. Soc. 1981, 22, 1037. Coxon, J. M.; Simpson, G. W.; Steel, P. J.; Trenerry, V. C. J. Am. Chem. Soc. 1983, 24, 1427. Indirect method for preparation of epoxides from homoallyl alcohols, see: Bartlett, P. A.; Jernstedt, K. K. J. Am. Chem. Soc. 1977, 99, 4829.
4. uanti” according to the definition of Masamune: Masamune, S.; Ali, S. A.; Snitman, D. L.; Garvey, D. S. Angew. Chem., Int. Ed. Engl. 1980, 19, 557. Masamune, S.; Kaiho, T.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5521.
5. Hasan, I.; Kishi, Y. Tetrahedron Lett. 1980, 21, 4229 Tomioka, H.; Suzuki, T.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982. 23, 3387. Narula, A. S. Tetrahedron Lett. 1982, 23, 5579.
6. Sato, F.; Tanaka, Y.; Sato, M. J. Chem. Soc., Chem. Commun. 1983, 165.
7. Recent publications in this area, see: (a) Masamune, S.; Hirama, M.; Mori, S.; Asrof, Sk.; Garvey, D. S. J. Am. Chem. Soc. 1981, 103, 1568. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Stork, G.; Paterson, I.; Lee, F. K. C. J. Am. Chem. Soc. 1982, 104, 4686. (d) Vedejs, E.; Dolphin, J. M.; Mastalerz, H. J. Am. Chem. Soc. 1983, 105, 127. (e) Kinoshita, M.; Ohsawa, N.; Gomi, S. Carbohydr. Res. 1982, 109, 5. (0 Paterson, I. Tetrahedron Lett. 1983, 24, 1311. (g) Paterson, I.; Patel, S. K.; Porter, J. R. J. Am. Chem. Soc. 1983, 24, 3395. (h) Oikawa, Y.; Nishi, T.; Yonemitsu, O. J. Am. Chem. Soc. 1983, 24, 3635.
8. Rossiter, B. E.; Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 464.
9. Sato, F.; Ishikawa, H.; Sato, M. Tetrahedron Lett. 1981, 22, 85.
10. Heathcock, C. H.; Pirrung, M. C.; Montgomery, S. H.; Lampe, J. Tetrahedron 1981, 37, 4087.
11. Nakata, M.; Takao, H.; Ikeyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. Nakata, M.; Enari, H.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1982, 55, 3283. Nakata, T.; Fukui, M.; Ohtsuka, H.; Oishi, T. Tetrahedron 1984, 40, 2225. Corey, E. J.; Hase, T. Tetrahedron Lett. 1979, 335. Hungerbühler, E.; Seebach, D.; Wasmuth, D. Angew. Chem., Int. Ed. Engl. 1979, 18, 958. Wood, R. D.; Ganem, B. Tetrahedron Lett. 1982, 23, 707. Johnson, M. R.; Nakata, T.; Kishi, Y. Bull. Chem. Soc. Jpn. 1979, 4343. Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873. Mori, K.; Iwasawa, H. Bull. Chem. Soc. Jpn. 1980, 36, 87. Lipshutz, B. H.; Kozlowski, J. A. Bull. Chem. Soc. Jpn. 1984, 49, 1147. Ho, P.-T. Can. J. Chem. 1982, 60, 90. Inanaga, J.; Kawanami, Y.; Yamaguchi, M. Chem. Lett. 1981, 1415. Corey, E. J.; Trybulski, E. J.; Melvin, L. S., Jr.; Nicolaou, K. C.; Secrist, J. A.; Lett, R.; Sheldrake, P. W.; Falck, J. R.; Brunelle, D. J.; Haslanger, M. F.; Kim, S.; Yoo, S. J. Am. Chem. Soc. 1978, 100, 4618. Helbig, W. Ann. Chem. 1984, 1165. Roush, W. R.; Adam, M. A.; Peseckis, S. M. Tetrahedron Lett. 1983, 24, 1377. Suzuki, T.; Saimoto, H.; Tomioka, H.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 23, 3597. Pfaltz, A.; Mattenberger, A. Angew. Chem., Int. Ed. Engl. 1982, 21, 71.