Helvetica Chimica Acta p. 760 - 765 (1987)
Update date:2022-07-30
Topics:
Milenkov, Branimir
Guggisberg, Armin
Hesse, Manfred
The title compound was synthesized from 1-(3'-hydroxypropyl)-2-oxocyclododecane-1-carbonitrile (3), using two different routes (Scheme).The CN group of 3 was converted to the Me3N(1+) residue in 5 which underwent , upon NaH treatment, a fragmentation leading to the ring-enlargement product 6.Teh same product was observed after heating the ring-enlarged dimethylamine oxide 14, prepared from 3 bya Bu4NF treatment and conversion of the CN into the dimethylamine-oxide moniety.Ozonolysis of the methylidene double bond in 6 and reduction of the resulting C=O to a CH2 group gave Exaltolide<*> (8).
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