Electrochemical Dearomative Dihydroxylation and Hydroxycyclization of Indoles
International audience
Recent Advances on the C2-Functionalization of Indole via Umpolung
Published in Topics in Current Chemistry
Heterocyclic compounds having a nitrogen atom in the ring exhibit very interesting biological activities. Indole is the core structure of many bioactive compounds owing to its high affinity to bind with most biological targets. Indole is an electron-rich compound and generally prefers electrophilic rather than nucleophilic substitution. Hence, many...
Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.
...Published in Angewandte Chemie (International ed. in English)
A biomimetic route to farnesyl pyrophosphate and dimethyl orsellinic acid (DMOA)-derived meroterpenoid scaffolds has yet to be reported despite great interest from the chemistry and biomedical research communities. A concise synthetic route with the potential to access DMOA-derived meroterpenoids is highly desirable to create a library of related c...
Sustainable Transformations of Methyl Coumalate : efficient Preparations of Unsaturated Carboxylic Acids, 2HPyrans, Trif...
In this work, we have described the development of new transformations using bio-based renewable methyl coumalate as feedstock. An iron and copper catalyzed one-pot sequential double alkyl-alkyl or alkyl-hydride 1,6-addition with methyl coumalate was described. We then described an efficient synthesis of tetrasubstituted 2H-pyrans under mild condit...
An efficient and facile synthesis of new tetracyclic fused pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-4(5H)-ones
Published in Molecular Diversity
Reaction of amidrazones 1a–1i with (1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)propanedinitrile (2) in ethyl acetate solution in one-step reaction led to the formation of unprecedented pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-4(5H)-ones 3a–3g along with pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-12b-oles 3h–3m in moderate to e...
Hypercoordinate Iodine Catalysts in Enantioselective Transformation: The Role of Catalyst Folding in Stereoselectivity
The need for metal-free environmentally benign catalysts has provided a strong impetus toward the emergence of hypercoordinate iodine reagents. At this stage of development, molecular insights on the mechanism and origin of stereo selectivity are quite timely. In this study, the origin of stereoinduction in a class of iodoresorcinol-based chiral hy...
π(4)s + π(2)s Cycloaddition of Spiroepoxycyclohexa-2,4-dienone, Radical Cyclization, and Oxidation-Aldol-Oxidation Casca...
Published in The Journal of organic chemistry
Synthesis of a tetracyclic ring system (BCDE) of atropurpuran is described. Oxidative dearomatization, cycloaddition of spiroepoxycyclohexa-2,4-dienone, radical cyclization, and a tandem oxidation-aldol-oxidation are the key features of our methodology.
DFT studies on the palladium-catalyzed dearomatization reaction between naphthalene allyl chloride and allyltributylstan...
Published in Journal of Molecular Modeling
The Pd-catalyzed dearomatization of naphthalene allyl chloride with allyltributylstannane has been investigated using density functional theory (DFT) calculations at the B3LYP level. The calculations indicate that the (ŋ1-allyl)(ŋ3-allyl)Pd(PH3) complex is responsible for the formation of ortho-dearomatized product. Moreover it is easy to produce t...
Studies Towards the Leucetta-derived Alkaloids Spirocalcaridine A and B - Possible Biosynthetic Implications.
Published in European journal of organic chemistry
An exploration of an abiotic approach to spirocalcaridines A and B is described centered on electrophile-induced dearomatizing spirocyclization of aryl enyne derivatives. Elaboration of the α-iodoenone via an Ullmann-like, copper-catalyzed amidation provided a formamide which upon treatment with methylamine undergoes a dienol-arene rearrangement, p...
Désaromatisation oxygénante asymétrique de phénols à l'aide d'iodanes pour la synthèse totale de substances naturelles
La réaction de désaromatisation oxygénante de phénols est une transformation très utile en tant qu’étape clé dans la synthèse de substances naturelles complexes. Elle permet de préparer des intermédiaires de type cyclohexa-2,4-diénones à partir de phénols ortho-substitués, notamment en utilisant des réactifs iodés hypervalents (i.e., iodanes) qui c...
