Details
| Original language | English |
|---|---|
| Pages (from-to) | 3956-3959 |
| Number of pages | 4 |
| Journal | Organic letters |
| Volume | 22 |
| Issue number | 10 |
| Early online date | 5 May 2020 |
| Publication status | Published - 15 May 2020 |
| Externally published | Yes |
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.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
Sustainable Development Goals
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In: Organic letters, Vol. 22, No. 10, 15.05.2020, p. 3956-3959.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of Aspidodispermine via Pericyclic Framework Reconstruction
AU - Reuss, Franziska
AU - Heretsch, Philipp
N1 - Funding Information: Financial support for this work was provided by the Studienstiftung des Deutschen Volkes (Ph.D. scholarship to F.R.). Umicore is acknowledged for a generous gift of M711 metathesis catalyst. We are grateful to Xenia Hagemann, Mykhaylo Alekseychuk, and Merlin Kleoff (Freie Universität Berlin) for experimental assistance. The Core Facility BioSupraMol supported by the DFG is acknowledged.
PY - 2020/5/15
Y1 - 2020/5/15
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85084644452&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.0c01242
DO - 10.1021/acs.orglett.0c01242
M3 - Article
VL - 22
SP - 3956
EP - 3959
JO - Organic letters
JF - Organic letters
SN - 1523-7060
IS - 10
ER -