Dataset Information


Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C-H Borylation.

ABSTRACT: Verruculogen and fumitremorgin A are bioactive alkaloids that contain a unique eight-membered endoperoxide. Although related natural products such as fumitremorgins B and C have been previously synthesized, we report the first synthesis of the more complex, endoperoxide-containing members of this family. A concise route to verruculogen and fumitremorgin A relied not only on a hydroperoxide/indole hemiaminal cyclization, but also on the ability to access the seemingly simple starting material, 6-methoxytryptophan. An iridium-catalyzed C-H borylation/Chan-Lam procedure guided by an N-TIPS group enabled the conversion of a tryptophan derivative into a 6-methoxytryptophan derivative, proving to be a general way to functionalize the C6 position of an N,C3-disubstituted indole for the synthesis of indole-containing natural products and pharmaceuticals.


PROVIDER: S-EPMC4777340 | BioStudies | 2015-01-01

REPOSITORIES: biostudies

Similar Datasets

1983-01-01 | S-EPMC1152342 | BioStudies
1000-01-01 | S-EPMC3346476 | BioStudies
2015-01-01 | S-EPMC4804460 | BioStudies
2019-01-01 | S-EPMC6901024 | BioStudies
2009-01-01 | S-EPMC2654583 | BioStudies
2013-01-01 | S-EPMC3692361 | BioStudies
2013-01-01 | S-EPMC3593668 | BioStudies
2016-01-01 | S-EPMC4960981 | BioStudies
2018-01-01 | S-EPMC6200647 | BioStudies
2013-01-01 | S-EPMC3870192 | BioStudies