Flow chemistry-enabled asymmetric synthesis of cyproterone acetate in a chemo-biocatalytic approach
Nature Communications,
Год журнала:
2025,
Номер
16(1)
Опубликована: Янв. 27, 2025
Язык: Английский
Manganese-Catalyzed Mukaiyama Hydration Reaction for Undergraduate Organic Chemistry Course
Journal of Chemical Education,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 7, 2025
Язык: Английский
Manganese/Enzyme Sequential Catalytic Pathway for the Production of Optically Active γ-Functionalized Alcohols
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 9103 - 9109
Опубликована: Июнь 6, 2024
A
brief,
practical
catalytic
process
for
the
production
of
optically
active
γ-functionalized
alcohols
from
relevant
alkenes
has
been
developed
by
using
a
robust
Mn(III)/air/(Me2SiH)2O
system
combined
with
lipase-catalyzed
kinetic
resolution.
This
approach
demonstrates
exceptional
tolerance
toward
proximal
functional
groups
present
on
alkenes,
enabling
achievement
high
yields
and
exclusive
enantioselectivity.
Under
this
sequential
system,
chiral
alkene
precursors
can
also
be
converted
into
related
acetates
as
separable
single
enantiomers.
Язык: Английский
Single-cell enzymatic cascade synthesis of testolactone enabled by engineering of polycyclic ketone monooxygenase and multi-gene expression fine-tuning
International Journal of Biological Macromolecules,
Год журнала:
2024,
Номер
275, С. 133229 - 133229
Опубликована: Июнь 17, 2024
Язык: Английский
Flow Chemistry-Enabled Asymmetric Synthesis of Cyproterone Acetate: A Chemo-biocatalytic Approach
Research Square (Research Square),
Год журнала:
2024,
Номер
unknown
Опубликована: Авг. 21, 2024
Abstract
Flow
chemistry
has
many
advantages
over
batch
synthesis
of
organic
small-molecules
in
terms
environmental
compatibility,
safety
and
synthetic
efficiency
especially
when
scale-up
is
considered.
However,
its
application
manufacturing
active
pharmaceutical
ingredients
(APIs)
still
rare
due
to
the
complexity
involved
with
operating
a
multistep
continuous
reaction
sequence.
As
demonstration
an
alternative
approach
steroid
chemistry,
herein,
we
report
first
10-step
chemo-biocatalytic
flow
asymmetric
cyproterone
acetate
(4)
which
10
transformations
are
combined
into
telescoped
linear
sequence
from
commercially
available
4-androstene-3,
17-dione
(11).
This
integrated
one-flow
features
engineered
3-ketosteroid-Δ1-dehydrogenase
(ReM2)-catalyzed
Δ1-dehydrogenation
form
C1,
C2-double
bond
A
ring,
substrate-controlled
Co-catalyzed
Mukaiyama
hydration
Δ1,
4,
16-triene-3,
20-dione
9
forge
crucial
chiral
C17α-OH
group
D
ring
excellent
stereoselectivity,
rapid
Corey-Chaykovsky
cyclopropanation
17α-hydroxy-Δ1,
6-triene-3-one-20-ketal
7
build
cyclopropyl
core
ring.
By
strategic
use
these
three
key
reactions
fully
continuous-flow
operations,
was
produced
overall
yield
9.65%
3
h
total
time,
this
shortest
route
steroid,
highest
number
chemical
transformation
performance
any
other
reported
date.
Also
included
Ni-catalyzed
batch-mode
nucleophilic
using
DCM
as
methylene
source
for
formation
disubstituted
three-membered
on
steroids
chemo-regio-diastereoselectivity.
Язык: Английский
Improving the bioconversion of phytosterols to 9α-hydroxy-4-androstene-3,17-dione by disruption of acyltransferase SucT and TmaT associated with the mycobacterial cell wall synthesis
World Journal of Microbiology and Biotechnology,
Год журнала:
2024,
Номер
40(11)
Опубликована: Окт. 15, 2024
Язык: Английский