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

Jarosz S., Jędra S.

Polish Journal of Chemistry

2009

Vol. 83, nr 10

1757-1764

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.