Functionalization of the Homoallylic Bridge in Higher Sugar Precursors

• Autorzy: Jarosz S. , Szewczyk K. , Gaweł A. , Gomez A. , Lopez J.
• Języki publikacji: EN

Abstrakty

EN

The Barton reduction of the sugar homoallylic xanthate did not afford the expected hydrocarbon, but led to two cyclic products resulting from the attack of initially formed radical onto the olefin fragment of the homoallylic system. The mechanism of such cyclization is discussed.

Słowa kluczowe

EN

higher sugar; homoallylic alcohols; rearrangement; cyclization

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 2
• Strony: 231--238
• Opis fizyczny: Bibliogr. 19 poz., rys.

Twórcy

autor

Jarosz S.

• Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland

autor

Szewczyk K.

• Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland

autor

Gaweł A.

• Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland

autor

Gomez A.

• Instituto de Quimica Orgánica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain

autor

Lopez J.

• Instituto de Quimica Orgánica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain

Bibliografia

• 1.Takatsuki A., Arima G. and Tamura J., .J. Antibiot, 24, 215 (1971).
• 2. Wolfrom M.L., Binkley W.W., Spencer C.C. and Lew B.W., J. Am. Chem. Soc., 73, 3357 (1951).
• 3. Perrier R.J. and Prasad N., .J. Chem. Soc. C., 589 (1969).
• 4. Roy R.B. and Chilton W.S., J. Org. Chem., 36, 3242 (1971).
• 5. Paulsen H., Roden K., Sinwell V. and Koebernick W., Angew Chem, 88, 477 (1976).
• 6. Secrist III J.A. and Barnes K.D., J. Org. Chem., 45, 4526 (1980); Secrist III J. A., Barnes K.D. and Wu Sh.-R., Trends Carbohydr: Chem., 386, 93 (1989; ACS Symposium Series, Horton D., Hawkins D. L. and McGarvey G. J. Eds.).
• 7. Fukuda Y., Sasai H. and Suami T., Bull. Chem. Soc. Jpn, 54, 1830 (1981).
• 8. The literature (up to 1997) on the preparation of higher carbon sugars is covered in a book: Gyorgydeak Z. and Pelyvas I.., Monosaccharide sugars: chemical synthesis by chain elongation, degradation and epimerization (Academic Press, 1998); some new references: Marquis Ch., Picasso S., and VogelP., Synthesis, 1441 (1999); Blackwell H.E., O’Leary D.J., Chatterjee A.K., Washenfelder R.C., Bussmatm D.A. and Grubbs R.H., J. Am. Chem. Soc., 122, 58 (2000); Shuto S., Terauchi M., Yahiro Y., Abe 1-1., lchikawa S. and Matsuda A., Tetrahedron Lett., 41, 4151 (2000); Jarosz S., J. Carbohydt: Chem., 20, 93 (2001). Engers D.W., Bassindale M.J. and Pagenkopf B.L., Org. Lett., 6, 663 (2004) and references therein; Liu Y. and Gallagher T., Org. Lett., 6, 2445 (2004) and references therein; Kroger L., Henkensmeier D., Schafer A., and Thiem J., Bioorg. Med. Chem. Lett., 14, 73 (2004); Cook M.J., Fletcher M.J.E., Gray D., Lovellb P.J. and Gallagher T., Tetrahedron, 60, 5085 (2004).
• 9. Ramza J. and Zamojski A., Tetrahedron, 48, 6123 (1992); Ramza J. and Zamojski A., Carbohydr Res., 22a, 205 (1992).
• 10. Karpiesiuk W. and Banaszek A., Carbohydr Res., 299, 245 (1997).
• 11. Jarosz S., Skora S., Szewczyk K. and Ciunik Z., Tetrahedron: Asymmetry, 12, 1895 (2001).
• 12. Jarosz S., Szewczyk K., Luboradzki R. and Gawel A., Tetrahedron: Asymmetry, 15, 1719 (2004).
• 13.Barton D.H.R. and McCombie S.W., J. Chem. Soc., Perkin Trans. 1, 1574 (1975); Barton D.H.R., Motherwell W.B., in Organic Synthesis Today and Tomorrow, (Trost B.M. and Hutchinson C.R. Eds, Pergatnon, Oxford, 1981); review on the Barton-McCombie reaction: Crich D. and Quintero L., Chem. Rev., 89, 1413 (1989) and references therein.
• 14. Roush W.R. and Brown B.B., J Am. Chem. Soc., 115, 2268 (1993).
• 15.Rhee I.U., Bliss B.I. and Rajan Babu T.V., J. Am. Chem. Soc., 125, 1492 (2003); cylization of the homopropragylic alcohols see: Angoh A.G. and Clive D.L., .I. Chem. Soc., Chem. Comm., 980 (1986).
• 16. Tarnaru Y., Mizutani M., FurukawaY., Kawamura Sh.-i., Yoshida Z.i., Yanagi K. and Minobe M., J. Am. Chem. Soc., 106, 1079 (1984); see also: Rassu G., Pinna L., Spanu P., Zanardfi F., Battistini L. and Casiraghi G., .J Org. Chem., 62, 4513 (1997).
• 17. Zunszain P. and Varela O., Tetrahedron: Asymmetry, 11, 765 (2000).
• 18. Barrett A.G.M. and Lee A.C., J. Org. Chem., 57, 2818 (1992).
• 19. Rao A.V.R., Roddy K.A., Gurjar M.K. and Kunwar A.C., J. Chem. Soc., Chem. Comm., 308 (1988).