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http://yadda.icm.edu.pl:80/baztech/element/bwmeta1.element.baztech-article-BUJ7-0015-0085

Czasopismo

Polish Journal of Chemistry

Tytuł artykułu

Synthesis of Complex Bicyclo[4.3.0]nonene Derivatives from Sugar Allyltins; Sugar Mimetics Derived from D-Glucose

Autorzy Jarosz, S.  Jędra, S. 
Treść / Zawartość
Warianty tytułu
Języki publikacji EN
Abstrakty
EN Controlled decomposition of sugar allyltin: methyl 2,3,4-tri-O-benzyl- 6,7,8- tri -deoxy-8-(tri-n-butyl)stannyl-alfa-D-gluco-oct-6(E)-eno-hexo-1,5-pyranoside af forded the corresponding dienoaldehyde with the D-xylo-configuration and the E-geometry across the internal double bond. Reaction of this intermediate with Ph3P=CH-CO2Me provided a triene, which under went cyclization to the bicyclic products: derivatives of bicyclo[4.3.0]nonatriene. Stereochemical aspects of this cyclization, as well as some transformations leading to carbobicyclic sugar mimics, are discussed.
Słowa kluczowe
EN sugar allyltin derivatives   cyclization   Diels-Alder reaction   stereochemistry  
Wydawca Polskie Towarzystwo Chemiczne
Czasopismo Polish Journal of Chemistry
Rocznik 2009
Tom Vol. 83, nr 10
Strony 1757--1764
Opis fizyczny Bibliogr. 11 poz., rys.
Twórcy
autor Jarosz, S.
autor Jędra, S.
  • Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland, sljar@icho.edu.pl
Bibliografia
1. Suami T. and Ogawa T, Adv. Carbohydr. Chem., Biochem., 48, 22 (1990); Arjona O., Gomez A.M., Lopez J.C. and Plumet J., Chem. Rev., 107, 1919 (2007).
2. Mehta G. and Ramesh S.S., Chem. Commun., 2429 (2000); Mehta G. and Ramesh S.S., Tetrahedron Lett., 42, 1987 (2001); Mehta G. and Ramesh S.S., Can. J. Chem., 83, 581 (2005).
3. Herczegh P., Zsely M., Szilagyi L., Bajza I., Kovacs A., Barta G. and Bognar R., Cycloaddition Reactions in Organic Chemistry, 112 (1992) (ACS Symposium Series 494, Guiliano R.M. Edition).
4. Hanessian S., Total Synthesis of Natural Products: The Chiron Approach, Pergamon Press, New York, 1983; Fraser-Reid B., Acc. Chem. Res., 29, 57 (1996).
5. For a review see: Jarosz S. and Gaweł A., Eur. J. Org. Chem., 3415 (2005).
6. Pindur U., Lutz G. and Otto Ch., Chem. Rev., 93, 741 (1993).
7. See for example: Roush W.R., Advances in Cycloaddition, 2, 91 (1990) and references therein; Deagostino A., Maddaluno J., Prandi C. and Venturello P., J. Org. Chem., 61, 7597 (1996); Gwaltney II S.L., Sakata S.T. and Shea K.J., J. Org. Chem., 61, 7438 (1996).
8. Kozłowska E. and Jarosz S., J. Carbohydr. Chem., 13, 889 (1994).
9. Jarosz S., Kozłowska E. and Jeżewski A., Tetrahedron, S3, 10775 (1997).
10. Jarosz S., Boryczko B., CmochR, Gomez A.M. and Lopez C, Tetrahedron: Asymmetry, 16,513 (2005).
11. Jarosz S., Szewczyk K. and Zawisza A., Tetrahedron: Asymmetry, 14, 1709 (2003); ibid, item, 14,1715 (2003).
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