Synthesis,
Journal Year:
2022,
Volume and Issue:
55(09), P. 1367 - 1374
Published: Nov. 15, 2022
Abstract
We
report
the
visible
light
photocatalytic
cleavage
of
trityl
thioethers
or
ethers
under
pH-neutral
conditions.
The
method
results
in
formation
respective
symmetrical
disulfides
and
alcohols
moderate
to
excellent
yield.
protocol
only
requires
addition
a
suitable
photocatalyst
rendering
it
orthogonal
several
functionalities,
including
acid
labile
protective
groups.
same
conditions
can
be
used
directly
convert
trityl-protected
thiols
into
unsymmetrical
selenosulfides,
cleave
resins
solid
phase
organic
synthesis.
Natural Product Reports,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
We
describe
the
pipeline
of
anticancer
agents
from
marine
cyanobacteria,
highlighting
critical
steps
discovery
towards
development,
including
identification
molecular
target
and
mechanism
action,
solving
supply
problem.
Marine Drugs,
Journal Year:
2024,
Volume and Issue:
22(9), P. 426 - 426
Published: Sept. 20, 2024
Marine
natural
products
comprise
unique
chemical
structures
and
vast
varieties
of
biological
activities.
This
review
aims
to
summarize
halichondrin,
a
marine
product,
its
synthetic
analogs
along
with
therapeutic
properties
mechanisms.
Halichondrin
analogs,
derived
from
sponges,
exhibit
potent
antineoplastic
properties,
making
them
promising
candidates
for
cancer
therapeutics.
These
compounds,
characterized
by
their
complex
molecular
structures,
have
demonstrated
significant
efficacy
in
inhibiting
microtubule
dynamics,
leading
cell
cycle
arrest
apoptosis
various
lines.
Several
types
halichondrins
such
as
B,
C,
norhalichondrin
homohalichondrin
B
been
discovered
similar
anticancer
antitumor
characteristics.
Since
naturally
available
show
hurdles
synthesis,
recent
advancements
methodologies
enabled
the
development
several
halichondrin
E7389
(eribulin),
which
shown
improved
indices.
Eribulin
has
excellent
immunomodulatory
mechanisms
reprogramming
tumor
microenvironments,
facilitating
infiltration
activation
immune
cells,
dynamics.
Despite
results,
challenges
remain
synthesis
clinical
application
these
compounds.
explores
underlying
activity
therapy,
applications
potential
future
drug
development.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(45)
Published: Oct. 16, 2023
Abstract
The
addition
of
carbon
electrophiles
to
carbonyls
and
imines
has
emerged
as
a
valuable
strategy
for
the
construction
C−C
bonds.
merger
this
concept
with
sustainable
cobalt
catalysis
yielded
numerous
innovative
methodologies.
Remarkable
functional
group
tolerance
selectivity
have
been
observed
in
many
cases,
providing
reliable
methods
bond
construction.
cobalt‐catalyzed
additions
carbonyls,
carboxylic
acid
derivatives
described
review
include
earliest
reports,
such
Takai‐Utimoto
Co/Cr
co‐catalyzed
their
progression,
well
modern
variants,
exemplified
by
recent
Co/photoredox
protocols.
systematic
appraisal
provides
clearer
perspective
inspiration
its
further
development.
Nature Communications,
Journal Year:
2023,
Volume and Issue:
14(1)
Published: April 5, 2023
Abstract
Eribulin
(Halaven)
is
the
most
structurally
complex
non-peptidic
drug
made
by
total
synthesis
and
has
challenged
preconceptions
of
synthetic
feasibility
in
discovery
development.
However,
despite
decades
research,
manufacture
eribulin
remains
a
daunting
task.
Here,
we
report
syntheses
fragment
(C14–C35)
used
two
distinct
industrial
routes
to
this
important
anticancer
drug.
Our
convergent
strategy
relies
on
doubly
diastereoselective
Corey–Chaykovsky
reaction
affect
union
tetrahydrofuran-containing
subunits.
Notably,
process
exclusively
enantiomerically
enriched
α-chloroaldehydes
as
building
blocks
for
constructing
three
densely
functionalized
oxygen
heterocycles
found
C14–C35
all
associated
stereocenters.
Overall,
can
now
be
produced
52
steps,
which
significant
reduction
from
that
reported
both
academic
syntheses.
Marine Drugs,
Journal Year:
2025,
Volume and Issue:
23(2), P. 69 - 69
Published: Feb. 7, 2025
Marine
organisms
represent
a
source
of
unique
chemical
entities
with
valuable
biomedical
potentialities,
broad
diversity,
and
complexity.
It
is
essential
to
ensure
reliable
sustainable
supply
marine
natural
products
(MNPs)
for
their
translation
into
commercial
drugs
other
products.
From
structural
point
view
few
exceptions,
MNPs
pharmaceutical
importance
derive
from
the
so-called
secondary
metabolism
organisms.
When
production
strategies
rely
on
macroorganisms,
harvesting
or
culturing
coupled
extraction
procedures
frequently
remain
only
alternative
producing
these
compounds
an
industrial
scale.
Their
can
often
be
implemented
laboratory
scale
cultures
bacterial,
fungal,
microalgal
sources.
However,
diverse
approach,
combining
traditional
methods
modern
synthetic
biology
biosynthesis
strategies,
must
considered
invertebrate
MNPs,
as
they
are
usually
naturally
accumulated
in
very
small
quantities.
This
review
offers
comprehensive
examination
various
addressing
challenges
related
supply,
synthesis,
scalability.
also
underscores
recent
biotechnological
advancements
that
likely
transform
current
industrial-scale
manufacturing
pharmaceuticals
derived
Natural Product Reports,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
Covering:
2000
to
2024The
cycloaddition
of
nitrile
oxides
with
olefins
(NOC),
followed
by
reductive
cleavage
the
resulting
isoxazolines,
has
been
widely
recognised
as
a
convenient
and
powerful
synthetic
strategy
for
constructing
aldol
motif
in
natural
product
synthesis.
Different
modes
NOC
(intermolecular,
fused
bridged
intramolecular)
enable
synthesis
diverse
isoxazoline
products,
which
can
be
converted
into
highly
substituted
cyclic
acyclic
frameworks.
This
review
examines
advances
this
field
over
past
25
years.
More
than
50
total
syntheses
are
discussed,
encompassing
various
classes
compounds,
including
macrolides,
alkaloids,
terpenoids,
steroids,
pseudosugars,
sulfolipids
some
others.
Moreover,
basic
aspects
methodology
outlined,
methods
generation
ring
cleavage,
well
stereochemical
models
intramolecular
oxide
cycloaddition.
Organic Syntheses,
Journal Year:
2024,
Volume and Issue:
unknown, P. 1 - 16
Published: Aug. 1, 2024
Abstract
This
chapter
presents
the
procedure
for
visible‐light‐mediated
oxidative
debenzylation
of
3‐O‐benzyl‐1,2:5,6‐
di‐O‐isopropylidene‐α‐d‐glucofuranose
.
Benzyl
ethers
are
important
protective
groups
in
synthesis
carbohydrates
due
to
their
excellent
stability
over
a
wide
range
conditions.
However,
benzyl
ether
cleavage
requires
harsh
reduction/oxidation
processes,
such
as
catalytic
hydrogenolysis,
Birch
reduction,
or
oxidation
with
ozone
BCl,
that
hazardous,
and
poorly
functional
group
tolerant.
The
photooxidative
strategy
overcomes
current
limitations
protecting
arise
from
conditions
necessary
cleavage.
methodology
enables
use
orthogonal
is
installed
removed
throughout
complex
molecules
clears
path
development
new
synthetic
routes
total
synthesis.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
27(4), P. 927 - 931
Published: Dec. 31, 2024
An
entirely
chromium-free
synthesis
of
eribulin,
a
fully
synthetic
macrocyclic
ketone
analogue
the
marine
natural
product
halichondrin
B,
was
achieved
through
iterative
sulfone
fragment
couplings
followed
by
an
intramolecular
Prins
reaction
involving
C.26
homoallenyl
alcohol
and
C.27
aldehyde
acetal.
A
notable
feature
this
new
macrocyclization
is
employment
β-ketosulfone
at
C.15/14
as
acid-stable
progenitor
notoriously
acid-sensitive
polycyclic
ketal
moiety,
characteristic
halichondrins.
