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Extra info for Chemical Reaction in the Interferometer U-Gauge
Knight 34 ether effect. Displacement by azide usually was the most efficient. Thus, exposure of iodotetrahydrofuran 27 to sodium azide in DMF at 80~ for 2h gave the inverted azide 121 in 87% isolated yield <99JCS(P1)2143>. Subsequent hydrogenation in the presence of Boc anhydride <89TL837> then delivered a good yield of the protected amine 122. Stronger heating gave substantial amounts of the elimination product, the 2,5-dihydrofuran 123. Displacement by an oxygen nucleophile could be effected using caesium acetate in hot DMF <81JOC4321> to give acetate 124 in moderate yield; the use of potassium superoxide and 18-crown-6 also in DMF <75CC658> gave marginally better yields of the corresponding alcohol, typically 60-70% at most.
The relatively low levels of stereoselection in cyclizations of the foregoing examples of 'anti'-(E)-homoallylic alcohols can also be addressed by using the very bulky aryl selenide 145 <95JOC3572>; levels are increased to 49:1 using this novel reagent. SePh " = ,,E Z Z 'syn' 95 141 \ 142 Z ...... SePh ~E ...... 'anti' 98 -.. " OH Z 143 r 145 Z 144 A number of studies have also been carried out to assess the impact of potentially more interactive substituents on such selenocyclizations. Landais has suggested that steric effects are probably responsible for the predominant formation of diastereoisomers 147 from alkenols 146 <95TL2987; 95SLl191>.
Preliminary results also indicate that the corresponding N-Boc derivatives undergo similarly smooth iodocyclizations. This methodology should prove useful for the synthesis of annulated pyrroles, exemplified D. W. Knight 46 by a synthesis of the bicyclic core 246 of the antitumor antibiotic Roseophilin, by radicalmediated cyclization of the iodopyrrole 245 and oxidation <99TL6117>.