Biomedical Engineering Reference
In-Depth Information
SCHEME 9.4
Overview of the folding pathway strategy in which alternative substrates are
converted into alternative scaffolds under common reaction conditions.
Oguri and Schreiber exploited Rh-catalyzed tandem cyclizations/cycloaddition
methodology
in
the
synthesis
of
alternative
indole
alkaloid-like
skeletons
(Scheme 9.5) [23]. An
-keto-carbonyl group and an indole ring were strate-
gically placed at different positions on the scaffolds of the starting materials (
21
to
23
). The substrates,
21
to
23
, were treated with a catalytic amount of rhodium(II)
-diazo-
SCHEME 9.5
Folding pathway based on tandem cyclization-cycloaddition chemistry lead-
ing to skeletally diverse alkaloid-like small molecules. Conditions: Catalytic Rh
2
(O
2
CC
7
H
15
)
4
,
benzene, 50
â—¦
C.
