ISSN:
1434-193X
Keywords:
Paclitaxel (Taxol®)
;
Paclitaxel CD-ring
;
High-pressure Diels-Alder reactions
;
Furan cycloadditions
;
Ether cleavage in 7-oxabicyclo[2.2.1]heptanes
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The high-pressure promoted Diels-Alder reactions between several furans and citraconic anhydride have been studied and the cycloadducts obtained have been explored in new straightforward routes to the CD-ring fragment of paclitaxel. The reaction between furan and citraconic anhydride afforded the exo cycloadduct diastereoselectively, whereas a variety of 2-substituted furans afforded approximate 1:1 mixtures of exo regioisomers. Separation of both regioisomers was accomplished after either diastereoselective esterification or regioselective reduction of the anhydride function. Ether cleavage of the bicyclic compounds by either high-pressure promoted ether cleavage or Boord elimination afforded several potential CD-ring precursors which can be used in the total synthesis of paclitaxel analogues.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
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