Application of the principles of synthesis design to the problem of prostaglandins led to many possible routes, including one commencing with endo-dicyclopentadiene. This starting material was then converted into racemic prostaglandin FZa in a minimum of ten stages via bicyclo [3.3.0]octane intermediates.
Hull HU8 7DSThe reactions of 1 -nitroso-2-naphthol with 1 -morpholinocyclohexene and 1 -rnorpholinopropene give the dihydrooxazine derivatives (1 ; X = OH) and (2). respectively. Attempts to extend the reaction to a variety of enamines and 1 -nitroso-2-phenols have been unsuccessful.
The reaction between cyclohexanone enamines and a variety of benzylidene ketones gives a dihydropyran derivative in each case. The benzopyrans from reactions of 1 -piperidinocyclohexene with chalcone and with dibenzylideneacetone are unstable and on heating readily rearrange into isomeric enamino-ketones (6) and (1 0). Recyclisation of 2-phenyl-2-(2-piperidinocyclohex-2-enyl)ethyl styryl ketone (1 0) gives 1.4-diphenyl-7b-piperidinoperhydrocyclobuta[de] naphthaten-2-one (1 1 ).
Bei der Reaktion der Enamine (I) mit Nitrosobenzol (III) bilden sich die Hydroxylamine (III); während sich das kristalline (IIIb) als stabil erweist, lagert sich das ölige (IIIa) beim Stehen in das Cyclohexylidenanilin (IV) um.
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