ISSN:
1434-193X
Keywords:
Taxol
;
Nitrile oxide
;
Cycloaddition reactions
;
Isoxazoline
;
Cyclopropane
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The intramolecular nucleophilic substitution of an epoxide by the anion of a nitrile was used to construct the bicyclo[3.1.0]hexane system of 9, derived from 8, and of 14, derived from 13. The intramolecular 1,3-dipolar cycloaddition of nitrile oxide 4, obtained from 14, led to isoxazoline 3. However, it was not possible to convert 3 into the corresponding β-hydroxy ketone. Rearrangements of 3 were observed in the presence of dehydrating reagents leading to compounds 19-21, which are structurally related to 11(15→1)abeotaxanes.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
Permalink