Abstract
Inositol phosphate derivatives are usually synthesized by repeated
protection-deprotection procedures, necessitating development of
an independent synthetic route for each inositol derivative. Herein,
a synthetic precursor for all regioisomers of inositol phosphate
is reported. A cycloadduct obtained by the Diels-Alder reaction
of trans -1-methoxy-3-trimethylsilyloxybuta-1,3-diene
and methyl vinyl ketone was converted into an inositol derivative
by sequential introduction and immediate protection of hydroxy groups. Thus,
the six hydroxy groups of the obtained inositol derivative are differentiated
by different protective groups that are cleavable under independent
conditions. This would enable us to prepare all regioisomers of
inositol phosphate derivative.
Key words
inositol phosphate - Diels-Alder reaction - oxidative rearrangement - asymmetric dihydroxylation
- monoacylation
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