Enantiospecific Synthesis of the 14-Membered Diene Unit of Methyl Sarcophytoate

Synlett

Volumn 1997, Issue 8, 1997, Pages 899-902

  Yasuda, Minoru ^a   Ide, Mitsuaki ^a   Matsumoto, Yuka ^a   Nakata, Masaya ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009531605     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-967     Document Type: Article

References (31)

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12. 1H NMR analysis of the derived (R)- and (S)-MTPA esters.
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17. For the recent examples, see: (a) Prandi, C.; Venturello, P. J. Org. Chem. 1994, 59, 3494-3496; (b) Nakatani, K.; Okamoto, A.; Yamanuki, M.; Saito, I. J. Org. Chem. 1994, 59, 4360-4361; (c) Majewski, M.; Irvine, N. M.; Bantle, G. W. J. Org. Chem. 1994, 59, 6697-6702.
18. For the recent examples, see: (a) Prandi, C.; Venturello, P. J. Org. Chem. 1994, 59, 3494-3496; (b) Nakatani, K.; Okamoto, A.; Yamanuki, M.; Saito, I. J. Org. Chem. 1994, 59, 4360-4361; (c) Majewski, M.; Irvine, N. M.; Bantle, G. W. J. Org. Chem. 1994, 59, 6697-6702.
19. For the recent examples, see: (a) Prandi, C.; Venturello, P. J. Org. Chem. 1994, 59, 3494-3496; (b) Nakatani, K.; Okamoto, A.; Yamanuki, M.; Saito, I. J. Org. Chem. 1994, 59, 4360-4361; (c) Majewski, M.; Irvine, N. M.; Bantle, G. W. J. Org. Chem. 1994, 59, 6697-6702.
20. t-BuOH was the best solvent to prevent hydrolysis of the acetonide.
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28. The unambiguous structure of 30b was confirmed by the X-ray crystallographic analysis. The details will be published in a full account.
29. 2Mg complex has been used, as a catalyst, for polymerization of monomers. For example, see: Kamienski, C. W.; Gastonia, N. C.; Eastham, J. F. U. S. Patent 3847883, 1974: Chem. Abstr. 1975, 82, 58590. The same complex has been used for metalation of substituted trifluoromethylbenzenes, see: Castaldi, G.; Borsotti, G. European Patent 0491326A2; Chem. Abstr. 1992, 117, 150667.
30. 2Mg complex has been used, as a catalyst, for polymerization of monomers. For example, see: Kamienski, C. W.; Gastonia, N. C.; Eastham, J. F. U. S. Patent 3847883, 1974: Chem. Abstr. 1975, 82, 58590. The same complex has been used for metalation of substituted trifluoromethylbenzenes, see: Castaldi, G.; Borsotti, G. European Patent 0491326A2; Chem. Abstr. 1992, 117, 150667.
31. 6) δ=18.6, 20.2, 20.6, 21.4, 26.6, 26.6, 26.7, 28.2, 29.0, 39.3, 68.4, 80.0, 83.7, 84.2, 105.6, 113.2, 121.3, 124.3, 125.8, 134.5, 137.6, 138.9, 143.0.