2 research outputs found
Scalable Synthesis of the Amber Odorant 9-<i>epi</i>-Ambrox through a Biomimetic Cationic Cyclization/Nucleophilic Bromination Reaction
A novel biomimetic
nucleophilic bromocyclization reaction is used
in the key step of a new and straightforward synthesis of 9-<i>epi</i>-Ambrox, an organic compound of high interest and value
in the context of fragrances. This strategic reaction allows access
to 9-<i>epi</i>-Ambrox on a gram scale from a dienyne derivative,
easily available from geraniol, following a sequence of seven steps
(35% global yield) with just one purification process. Both enantiomers
of the molecule were obtained by a challenging enzymatic resolution
Synthesis of Cyclohexanones through a Catalytic Cationic Cyclization of Alkynols or Enynes
A novel procedure
for the synthesis of cyclohexanones from alkynol
or enyne derivatives through a cationic cyclization has been developed.
The key points to obtain the six-membered ring derivatives are the
use of starting materials containing a terminal alkyne, the use of
tetrafluoroboric acid as a promoter of the cationic cyclization, and
the appropriate selection of 1,1,1,3,3,3-hexafluoropropan-2-ol
(HFIP) as solvent. This strategy can be extended to the biomimetic
cationic cyclization of several terpene-derived polyenynes