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SCHEME 5.21 Domino cyclopropanation/Cope rearrangement of trienone 50 . (Adapted
from [26], with permission; copyright C
2009 American Chemical Society.)
After reaction optimization, this domino cyclopropanation/Cope rearrangement
sequence could be applied to the benzamide-containing trienone 53 to afford a sepa-
rable mixture of diastereomers 54a : 54b (1 : 1.4) in good overall yield (Scheme 5.22).
Based on this methodology, a library of hydroazulenoisoindoles was prepared
(Scheme 5.23) [25b]. Eight trienone analogs 55 , prepared as reported previously
[25a], were subjected to the domino cyclopropanation/Cope rearrangement sequence
and yielded a total of 10 cycloheptadiene analogs 56 (44 to 75%). Further struc-
tural diversity was introduced via Diels-Alder cycloadditions with six readily avail-
able dienophiles, affording 40 hydroazulenoisoindoles 57 as single diastereomers
(Table 5.14).
SCHEME 5.22 Domino cyclopropanation/Cope rearrangement of trieneone 53 . (Adapted
from [26], with permission; copyright C
2009 American Chemical Society.)
 
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