Synthesis of the Trans and Cis Higher Sugar Allylic Alcohols—Direct Precursors of Dodecoses

References

• Jarosz , S. 1992 . Carbohydr. Res. , 224 : 73 and references therein; b. M. P. Maguire, P. L. Feldman and H. Rapoporl, J. Org. Chan., 55, 948 (1990); c. D. H. R. Barton, S. D. Gero, B. Quiclet-Sire and M. Samadi, J. Chem. Soc., Parian Trans. I, 981 (1991); d. Y. Wang, S. A. Babirad and Y. Kishi, J. Org. Chem., 57. 468 (1992); e. T. Haneda, P. G. Goekjian, S. H. Kim and Y. Kishi, J. Org. Chem., 57, 490 (1992); f L. Lay, F. Nicotra, L. Panza, G. Russo and E. Caneva, J. Org. Chem., 57, 1304 (1992). For a review on macrolide antibiotics containing structures related to higher carbon sugars see, T. L. B. Boivin, Tetrahedron. 43, 3309 (1987)
   Web of Science ®Google Scholar
• Uchida , K. , Ichikawa , T. , Schimauchi , Y. , Ihikura , T. and Ozaki , A. 1971 . J. Antibiot. , 24 : 259 See for example hikizimycin:
   PubMedGoogle Scholar
• Jarosz , S. 1988 . Carbohydr. Res. , 183 : 209
   Google Scholar
• Cha , J. K. , Krist , W. J. and Kishi , Y. 1984 . Tetrahedron , 40 : 2247
   Web of Science ®Google Scholar
• Jarosz , S. 1988 . Carbohydr. Res. , 183 : 217
   Web of Science ®Google Scholar
• Tronchet , J. M. J. , Bonenfant , A. P. , Perret , F. , Gonzales , A. , Zumwald , J.-B. , Martinez , E. M. and Baechler , B. 1980 . Helv. Chun. Acta , 63 : 1181 see also S. Czernecki and J. M. Valery, J. Carbohydr. Chem., 5. 235 (1986)
   Google Scholar
• Wolfram , M. L. and Hanessian , S. 1962 . J. Org. Chem. , 27 : 1800
   Web of Science ®Google Scholar
• Kuivila , H. G. 1964 . Adv. Organomet. Chem. , 1 : 47 b. S. Jarosz, Carbohydr. Res., 166, 211 (1987); S. Jarosz, Tetrahedron Lea., 29, 1193 (1988)
   Google Scholar
• Jarosz , S. 1988 . Carbohydr. Res. , 183 : 201
   Web of Science ®Google Scholar
• Freudenburg , K. , Durr , W. and von Hochsteller , H. 1928 . Ber. , 61 : 1735
   Google Scholar
• The ionic nature of lithium acelylides14 makes this assumption reasonable
   Google Scholar
• Czernecki , S. and Valery , J. M. 1988 . J. Carbohydr. Chem. , 7 : 151 For the influence of the complexation on the addition of acetylene to dialdoses see
   Web of Science ®Google Scholar
• Since the covalent character of the C-Li bond in vinyllilhiums is significant,14a the complexation of aldehyde 4 by lithium is very unlikely. However, when this vinylliihium reagent (7a) reacted with 4 pre-complexed with zinc chloride, the amount of the S-isomer significantly increased (R:S ratio changed from 72:28 to 48:52)
   Google Scholar
• Wardell , J. L. 1982 . Comprehensive Organometallic Chemistry , Edited by: Wilkinson , G. Vol. 1 , 43 – 121 . Pergamon Press . b. A. Streitwieser, Jr., J. E. Williams, Jr., S. Alexandratos and J. M. McKelvey, J. Am. Chem. Soc., 98, 4778 (1976); c. A. Hinchliffe, J. Mol. Struct., 37, 145 and 289 (1977)
   Google Scholar
• Arrick , R. E. , Baker , D. C. and Horton , D. 1973 . Carbohydr. Res. , 26 : 441
   Web of Science ®Google Scholar
• Bowden , K. , Heilbron , I. M. , Jones , E. R. H. and Weedon , B. C. L. 1946 . J. Chem. Soc. , 39
   Google Scholar
• Nakata , T. , Tanaka , T. and Oshi , T. 1983 . Tetrahedron Lett. , 24 : 2653 T. Takahashi, M. Miyazawa and J. Tsui, ibid., 26. 5139 (1985
   Web of Science ®Google Scholar
• Jarosz , S. to be published
   Google Scholar