Bridged-Type Selective Intramolecular Nitrone–Alkene Cycloaddition: Computational Chemistry-Inspired Regioselectivity Control
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 4, 2025
A
regioselective
intramolecular
nitrone-alkene
cycloaddition
for
synthesizing
oxazabicyclo
ring-fused
indoles
is
reported.
Computational
studies
guided
the
development
of
optimal
conditions
using
In(OTf)3
as
a
Lewis
acidic
reagent.
This
method
demonstrates
broad
substrate
scope,
forming
seven-
and
eight-membered
carbocycles
with
various
substituents,
provides
versatile
route
to
complex
nitrogen-containing
scaffolds
potential
applications
in
medicinal
chemistry
total
synthesis
biologically
active
compounds.
Язык: Английский
A Short Synthesis of (−)‐6,7‐Secoagroclavine via Metal‐Free Reductive Coupling
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(13)
Опубликована: Фев. 16, 2024
Abstract
A
concise,
convergent,
and
enantioselective
synthesis
of
(−)‐6,7‐secoagroclavine,
a
pivotal
intermediate
in
the
both
clavine
ergot
alkaloids,
was
accomplished
from
derivative
renowned
Uhle's
ketone.
The
is
centered
on
metal‐free
reductive
coupling
tosylhydrazone
protected
4‐amino
ketone
commercially
available
2,2‐dimethylethenylboronic
acid,
which
used
as
four‐carbon
building
block.
This
novel
approach
directly
sets
stereochemistry
difficult‐to‐access
aryl
vinyl
methane
carbon
stereogenic
center
(−)‐6,7‐secoagroclavine.
Язык: Английский