DOI: 10.1039/A707534K
(Paper)
Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 397-406
Stereoselective construction of the key intermediate for the synthesis of the tetrahydropyranyl antifungal agents (+)-restricticin and (+)-lanomycin
(Note: The full text of this document is currently only available in the PDF Version )
Toshio Honda, Akiko Satoh, Toshio Yamada, Tomohisa Hayakawa and Kazuo Kanai
Abstract
Stereoselective construction of the key intermediate for the synthesis of naturally occurring antifungal agents, such as (+)-restricticin and (+)-lanomycin, has been achieved by employing a chelation-controlled aldol reaction of methyl α-methyltetronate with (R)-cyclohexylideneglyceraldehyde as a key step.
References
- R. E. Schwartz, C. Dufresne, J. E. Flor, A. J. Kempf, K. E. Wilson, T. Lam, J. Onishi, J. Milligan, R. A. Fromtling, G. K. Abruzzo, R. Jenkins, K. Glazomitsky, G. Bills, L. Zitano, S. M. Del Val and M. N. Omstead, J. Antibiot., 1991, 44, 463 CAS; O. D. Hensens, C. F. Wichmann, J. M. Liesch, F. L. VanMiddlesworth, K. E. Wilson and R. E. Schwartz, Tetrahedron, 1991, 47, 3915 CrossRef CAS; S. Matsukuma, T. Ohtsuka, H. Kotaki, H. Shirai, T. Sano, K. Watanabe, N. Nakayama, Y. Itezono, N. Fujiu, N. Shimma, K. Yokose and T. Okuda, J. Antibiot., 1992, 45, 151 CAS.
- J. O'Sullivan, D. W. Phillipson, D. R. Kirsch, S. M. Fisher, M. H. Lai and W. H. Trejo, J. Antibiot., 1992, 45, 306 CAS; D. W. Phillipson, J. O'Sullivan, J. H. Johnson, M. S. Bolgar and A. D. Kahle, J. Antibiot., 1992, 45, 313 CAS.
- S. Jendrzejewski and P. Ermann, Tetrahedron Lett., 1993, 34, 615 CrossRef CAS; T. Tsukuda, I. Umeda, K. Masubuchi, M. Shirai and N. Shimma, Chem. Pharm. Bull., 1993, 41, 1191 CAS.
- N. Chida, T. Tobe, M. Yoshinaga, K. Osaka and S. Ogawa, Carbohydr. Lett., 1996, 2, 47 Search PubMed.
- S. H. Kang and C. M. Kim, Synlett, 1996, 515 CrossRef CAS.
- I. Paterson and T. Nowak, Tetrahedron Lett., 1996, 37, 8243 CrossRef CAS.
- T. Honda, T. Hayakawa, H. Kondoh, A. Okuyama and M. Tsubuki, Chem. Lett., 1991, 1861 CAS; T. Honda, H. Kondoh, A. Okuyama, T. Hayakawa, M. Tsubuki and H. Nagase, Heterocycles, 1992, 33, 67 CAS; T. Honda, T. Yamada, T. Hayakawa and K. Kanai, Tetrahedron: Asymmetry, 1994, 5, 247 CrossRef CAS.
- T. Kametani, T. Katoh, M. Tsubuki and T. Honda, J. Am. Chem. Soc., 1986, 108, 7055 CrossRef CAS; T. Kametani, T. Katoh, J. Fujio, I. Nogiwa, M. Tsubuki and T. Honda, J. Org. Chem., 1988, 53, 1982 CrossRef CAS.