Biomedical Engineering Reference
In-Depth Information
O
TBSO
TBSO
HO
2
C
HN
H
2
HN
CbzHN
OH
Cl
OH
Pd(OH)
2
/C
TBDPSO
TBDPSO
443
444
Pinnaic acid
442
SCHEME 9.80
Synthesis of pinnaic acid
442
by Arimoto and coworkers.
cycloheptene amine. Further transformations led to (
þ
)-calystegine B
2
(
441
) in a 25%
overall yield.
In 1996, Arimoto et al. [174] isolated a new class of marine natural products
from the bivalve
Pinna muricata
and the black sponge
H. okadai
Kadota, which is
represented, for example, by pinnaic acid (
). This compound inhibits the cPLA
2
in vitro
with an IC
50
value of 0.2mM. More recently, they developed an efficient
domino-hydrogenation/cyclization protocol for the synthesis of
442
, which included
the saturation of an alkene, the removal of a CBZ-protecting group, the formation of a
cyclic imine/enamine, and a hydrogenation [175]. Hence, treatment of
442
443
with H
2
in
the presence of a catalytic amount of Pd(OH)
2
/C led to
in over 80% yield, while
the latter was eventually converted into the natural product
444
442
(Scheme 9.80).
A similar approach was also used by Tietze and coworkers for the synthesis of several
indole and ipecacuanha alkaloids [78,79].
REFERENCES
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