Synthesis of the Pentacyclic Core of Sanguinone B Enabled by Alkyne Functionalization
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 15, 2025
Sanguinones
A
and
B
are
recently
isolated
pyrroloiminoquinone
alkaloids
possessing
a
rare
C4
carboxylic
acid.
We
report
synthetic
approach
toward
the
full
carbon
nitrogen
pentacyclic
core
of
sanguinone
B,
with
correct
oxidation
at
C4.
Highlights
this
include
application
Larock/Buchwald-Hartwig
annulation
cascade
to
access
key
tricyclic
intermediate
alkyne
functionalization
using
Rh(I)
or
Cu(I)
catalysis
hindered
benzylic
ketones.
Язык: Английский
A Divergent Synthesis of Numerous Pyrroloiminoquinone Alkaloids Identifies Promising Antiprotozoal Agents
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(43), С. 29883 - 29894
Опубликована: Окт. 16, 2024
On
the
basis
of
a
streamlined
route
to
pyrroloiminoquinone
(PIQ)
core,
we
made
16
natural
products
spread
across
four
classes
biosynthetically
related
alkaloid
products,
and
multiple
structural
analogs,
all
in
≤8
steps
longest
linear
sequence
(LLS).
The
strategy
features
Larock
indole
synthesis
as
key
operation
five-step
methoxy-PIQ
intermediate.
Critically,
this
compound
was
readily
diverged
via
selective
methylation
either
(or
both)
imine-like
or
pyrrole
nitrogens,
which
then
permitted
further
divergence
by
Язык: Английский