DOI: 10.1039/A809983I
(Paper)
Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 783-788
Synthetic study of marine lobane diterpenes. Enantioselective syntheses of lobatrienolide and lobatrientriol from (+)-nopinone
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Michiharu Kato, Hiroshi Kosugi, Tsuyoshi Ichiyanagi and Osamu Yamabe
Abstract
The first enantioselective syntheses of highly oxygenated lobane diterpenes, (+)-lobatrienolide 4 and (+)-lobatrientriol 5, have been achieved, starting with (4R,5R)-1-acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene 10b which itself has been prepared from (+)-nopinone 7 as a versatile building block toward the asymmetric synthesis of natural products.
References
- (a) For reviews on marine natural products, see: D. Faulkner, Nat. Prod. Rep., 1984, 251, 551; 1986, 1; 1987, 539; 1988, 631; 1990, 269; 1991, 97; 1992, 323; 1993, 497; 1994, 355; 1995, 223; 1996, 75; 1998, 113 Search PubMed; (b) C. J. Moody and M. J. Davies, Studies in Natural Products Chemistry, ed. Atta-ur-Rahman, Elsevier, New York, 1992, vol. 10, pp. 201–239 Search PubMed.
- R. W. Dunlop and R. Wells, Aust. J. Chem., 1979, 32, 1345 CAS.
- Y. Gopichand and F. J. Schmitz, Tetrahedron Lett., 1978, 3641 CrossRef CAS.
- J. Shin and W. Fenical, J. Org. Chem., 1991, 56, 3153 CrossRef CAS.
- M. Iwashima, H. Nagaoka, K. Kobayashi and Y. Yamada, Tetrahedron Lett., 1992, 33, 81 CrossRef CAS.
- H. Kosugi, O. Yamabe and M. Kato, J. Chem. Soc., Perkin Trans. 1, 1998, 217 RSC.
- T. Kusumi, T. Hamada, M. O. Ishitsuka, I. Ohtani and H. Kakisawa, J. Org. Chem., 1992, 57, 1033 CrossRef CAS.
- T. Hamada, T. Kusumi, M. O. Ishitsuka and H. Kakisawa, Chem. Lett., 1992, 33 CAS.
- M. Kato, V. P. Kamat, Y. Tooyama and A. Yoshikoshi, J. Org. Chem., 1989, 54, 1536 CrossRef CAS.
- M. Kato, M. Watanabe, B. Vogler, B. Z. Awen, Y. Masuda, Y. Tooyama and A. Yoshikoshi, J. Org. Chem., 1991, 56, 7071 CrossRef CAS.
- M. Watanabe, B. Z. Awen and M. Kato, J. Org. Chem., 1993, 58, 3923 CrossRef CAS.
- (a) G. Vidari, G. Lanfranchi, P. Sartori and S. Serra, Tetrahedron: Asymmetry, 1995, 6, 2977 CrossRef CAS; (b) R. J. Sterling and D. Barasch, Tetrahedron Lett., 1987, 28, 1685 CrossRef.
- (a) R. O. Hutchins, B. E. Maryanoff and C. J. Milewski, J. Am. Chem. Soc., 1971, 93, 1793 CrossRef CAS; (b) C. F. Lane, Synthesis, 1975, 135 CrossRef CAS.
- For the analogous reduction of the ketone group, see refs. 6 and 10.
- B. M. Trost and G. S. Massiot, J. Am. Chem. Soc., 1997, 99, 4405.
- For the use of sodium enolates in DMF, see (a) H. Kotake, K. Inomata, S. Aoyama and H. Kinoshita, Chem. Lett., 1977, 73 CAS; (b) P. Brownbridge, I. Fleming, A. Pearce and S. Warren, J. Chem. Soc., Chem. Commun., 1976, 751 RSC.