The first episode of lung surgery for pulmonary metastases of CRC was associated with very low mortality and reoperation rates (<1%). The postoperative morbidity rate was 16%. Independent risk factors of postoperative morbidity were major lung resection and respiratory and/or cardiovascular co-morbidity. Video-assisted surgery showed a protective effect.
protons, confirming its total reduction. Chromatography on alumina still did not permit crystallization, so the material was acetylated with pyridine and acetic anhydride. Prisms of racemic 0,N-diacetyldemethyldihydrogalanthamine were obtained which were recrystallized from ethyl acetate and sublimed at 150" (0.1 mm.), m.p. 208-209.5", [ o l I z 3~ 0.00,' [alZ3436 0.00' ( c 0.19, chloroform). The infrared spectrum in chloroform was identical with its optically active counterpart (m.p. 177-179'). Surprisingly, the compound does not appear t o depress the racemic 0,s-diacetyldemethylgalanthamine, m.p. 204-205', b u t fortunately its infrared spectrum ( K B r ) exhibits many points of difference.Conversion of Dihydronarcissamine to Racemic Dihydrogalanthamine.--4 solution of 150 mg. of the crude hydrogenation product of narcissamine in a mixture of 1 ml. of 9076 formic acid and 1 ml. of 3 i y G formalin was heated on the steam bath for 3 hr., basified, and extracted into chloroform. The product was then chromatographed over alumina with 1 YG ethanol in ethyl acetate and the resulting oil evaporatively distilled a t 150' (0.1 m m i . The infrared spectrum of the product is identical in chloroform solution with ( -)-dihydrogalanthamine and gas phase chromatography shows a retention time identical with the latter (see above). The material was purified by crystallizing its hydriodide salt from water, recovering the free base with alkali, and evaporatively distilling the product. Still an oil, the product showed [ a I z 3 D 0.0", [olIz3496 0.0" ( c 0.655, chloroform).Anal. Calcd. for C l i H~N 0 3 : C , 70.56; H , 8.01. Found: C, 70.32; H, 7.91.The compound formed a methiodide from acetone which was recrystallized from ethanol-water; m.p. 300' dec. The infrared spectrum ( K B r ) of the salt is very similar to, but not identical with, t h a t of ( -)-dihydrogalanthamine methiodide.(+)-Camphor was converted to (-))-homocamphor by known methods and in a short synthetic sequence the latter was transformed to the tricyclic cyclopentenone 10. Condensation with methylmagnesium iodide or with triphenylphosphinemethylene followed by hydrogenation yielded 8-patchoulene ( 12). Rearrangement of the corresponding epoxide 16 with boron fluoride furnished the desired unsaturated alcohol 18. This key intermediate was subsequently transformed to patchoulione ( 2 ) and to a-patchoulene (23). ' % previously accomplished b u t at t h a t time incorrectly interpreted reconversion of ol-patchoulene (23) to patchouli alcohol ( 2 8 ) completed the synthesis. Some transformations of the natural product 28 are reinterpreted in terms of a new structure determined by the X-ray method.
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