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

• Autorzy: Jarosz S. , Jędra S.
• 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,

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).