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Studies Directed Toward the Synthesis of Taxanes: Construction of the Tricyclo[5.3.1.0 1,7 ]undecane System
Author(s) -
Nivlet Alex,
Dechoux Luc,
Le Gall Thierry,
Mioskowski Charles
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199912)1999:12<3251::aid-ejoc3251>3.0.co;2-7
Subject(s) - nitrile , chemistry , intramolecular force , epoxide , bicyclic molecule , ketone , cycloaddition , nucleophile , undecane , reagent , nucleophilic addition , stereochemistry , medicinal chemistry , organic chemistry , catalysis
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.