From: Kerry Chappele (snoopz6969$##$yahoo.com)
Date: Tue Apr 13 2004 - 18:55:26 EDT
Hi...
I was wondering if anyone has had experience
synthesizing spiroketals that would be able to help me
formulate a proposal synthesis of the compound who
figure is attached.
I've been trying but I keep running into trouble
for a lot of the key transformations.
Here's a highlight of what I have tried:
-RCM
-Sugar starting material
-Diels-Alder
The problem is that this product is facing a ~2.5
kcal equilibrium between the other isomer which has 2
anomeric effects in its favor. So that means that the
key spirocyclic stereocenter has to be creatively
formed to avoid running into a thermodynamically
controlled reaction.
Thank you very much for any insight!
Kerry Chappele
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