Synthesis of Aspidodispermine via Pericyclic Framework Reconstruction
- authored by
- Franziska Reuss, Philipp Heretsch
- Abstract
A divergent approach to the pyrroloquinoline scaffold as present in the class of Aspidosperma alkaloids was developed. As a case study, abundant and renewable nicotinic acid was transformed via pericyclic framework reconstruction into aspidodispermine, a unique member of pyrroloquinoline alkaloids. The sequence comprises a [2 + 2]-photocycloaddition, a Ramberg-Bäcklund contraction, and a strain-promoted formal electrocyclic rearrangement of a bicyclo[2.2.0]hexene and is potentially extendable to pyrroloindole scaffolds as present in the ibophyllidine alkaloids.
- External Organisation(s)
-
Freie Universität Berlin (FU Berlin)
- Type
- Article
- Journal
- Organic letters
- Volume
- 22
- Pages
- 3956-3959
- No. of pages
- 4
- ISSN
- 1523-7060
- Publication date
- 15.05.2020
- Publication status
- Published
- Peer reviewed
- Yes
- ASJC Scopus subject areas
- Biochemistry, Physical and Theoretical Chemistry, Organic Chemistry
- Sustainable Development Goals
- SDG 7 - Affordable and Clean Energy
- Electronic version(s)
-
https://doi.org/10.1021/acs.orglett.0c01242 (Access:
Closed)
