Unknown

Dataset Information

0

Total synthesis of aristolactam alkaloids via synergistic C-H bond activation and dehydro-Diels-Alder reactions.


ABSTRACT: A concise total synthesis of aristolactam alkaloids by a synergistic combination of C-H bond activation and dehydro-Diels-Alder reactions is described. To achieve the synthesis two new synthetic methodologies, namely the oxidative cyclization of benzamides with vinyl sulfone leading to 3-methyleneisoindolin-1-ones via a ruthenium-catalyzed C-H bond activation, and a dehydro-Diels-Alder reaction followed by the fluoride ion mediated desulfonylation of 3-methyleneisoindolin-1-ones with benzynes, were developed. The method presented allows the opportunity for the construction of all the rings of aristolactams from easily available starting materials.

SUBMITTER: Reddy MC 

PROVIDER: S-EPMC6100235 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

altmetric image

Publications

Total synthesis of aristolactam alkaloids <i>via</i> synergistic C-H bond activation and dehydro-Diels-Alder reactions.

Reddy Mallu Chenna MC   Jeganmohan Masilamani M  

Chemical science 20170323 5


A concise total synthesis of aristolactam alkaloids by a synergistic combination of C-H bond activation and dehydro-Diels-Alder reactions is described. To achieve the synthesis two new synthetic methodologies, namely the oxidative cyclization of benzamides with vinyl sulfone leading to 3-methyleneisoindolin-1-ones <i>via</i> a ruthenium-catalyzed C-H bond activation, and a dehydro-Diels-Alder reaction followed by the fluoride ion mediated desulfonylation of 3-methyleneisoindolin-1-ones with benz  ...[more]

Similar Datasets

| S-EPMC4612511 | biostudies-literature
| S-EPMC6771859 | biostudies-literature
| S-EPMC3420159 | biostudies-literature
| S-EPMC4647982 | biostudies-literature
| S-EPMC8049058 | biostudies-literature
| S-EPMC2852147 | biostudies-literature
| S-EPMC6270290 | biostudies-literature
| S-EPMC2912946 | biostudies-literature
| S-EPMC7187354 | biostudies-literature
| S-EPMC4136723 | biostudies-literature