One-pot Nazarov cyclization/oxidative 1,2-carbon rearrangement/Ritter reaction to access 5-quaternary-4-amidocyclopent-2-enones and 2-quaternary-3-amidoindanones
Chemical Communications,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
A
one-pot
Nazarov
cyclization/oxidative
1,2-carbon
rearrangement/Ritter
reaction
has
been
explored
for
the
first
time,
facilitating
synthesis
of
unprecedented
2,3-disubstituted-5-quaternary-4-amidocyclopent-2-enone
and
2-quaternary-3-amidoindanones.
This
transformation
features
convenient
operation,
good
yields
(up
to
70%),
excellent
diastereoselectivity
20
:
1).
The
proposed
mechanism
is
supported
by
some
experimental
results.
Язык: Английский
Bioinspired Total Synthesis of 3-epi-Junipercedrol
Organic Letters,
Год журнала:
2024,
Номер
26(35), С. 7463 - 7467
Опубликована: Авг. 27, 2024
A
bioinspired
total
synthesis
of
3-epi-junipercedrol,
which
contains
a
strained
tricyclo[5.2.2.03,7]undecane
allo-cedrane
framework
and
five
stereocenters,
was
accomplished
via
an
effective
anionic
semipinacol
rearrangement
tricyclic
cedrane
mesylate.
The
corresponding
precursor
synthesized
efficiently
by
employing
the
reductive
oxy-Nazarov
cyclization
intramolecular
aldol
condensation
as
key
steps.
This
synthetic
approach
provided
further
evidence
for
biogenetic
relationship
between
typical
sesquiterpenoids.
Язык: Английский