ISSN:
0170-2041
Keywords:
Strychnopivotine
;
2-Azabicyclo[2.2.2]octanes
;
Isoquinuclidines
;
Cyclohexanone, 4-acetamido-
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Experiments Directed to the Synthesis of Strychnopivotine and a New Synthesis of the Isoquinuclidine FrameworkThe 2-azabicyclo[3.3.1]nonane (keto-morphane) 2 can be transformed via the enamine 4 into the dithio-dioxolane derivative 6 of the corresponding 6,7-diketone. After hydrolysis of the dithio group and formation of the monoprotected diketone 3 Fischer cyclisation yields the isodasycarpidone derivative 7, an intermediate to a synthesis of strychnopivotine (1a). - In view of the likewise desired tricyclus 8 for a synthesis of strychnopivotine, a cyclisation of ketoamide 9 was tried under standard conditions. By aldol-ring closure, however, not the expected 2-azabicyclo[3.3.1]nonane 14 was formed, but instead the 2-azabicyclo[2.2.2]octane derivative (isoquinuclidine) 15. The preparation of 9 via the intermediates 10-13 is described.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199219920182
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