Chromenone‐Fused Pyrrolizines and Pyrrolizine Analogues of Lamellarins: Expanding the Lamellarin Family
Abstract: Several N‐ethoxycarbonylmethyl enaminones, prepared by Eschenmoser sulfide contraction between N‐(ethoxycarbonylmethyl) pyrrolidine‐2‐thione and various ortho‐oxygenated phenacyl halides, underwent cyclisation to give ethyl 6‐aryl‐2,3‐dihydro‐1H‐pyrrolizine‐5‐carboxylates upon microwave heating with silica gel in xylene. With enaminones made from ortho‐hydroxyphenacyl halides, not only did dihydropyrrolizine formation take place, but spontaneous lactonisation also occurred to give 9,10‐dihydrochromeno[4,3‐b]pyrrolizin‐6 (8H)‐ones. Bromination and Suzuki‐Miyaura arylation of these chromenopyrrolizines at the free C−H site on the pyrrole ring afforded four analogues of the lamellarin alkaloids in which a pyrrolidine ring replaces the isoquinoline system in the fused polycyclic core. The product 11‐(3,4‐dimethoxyphenyl)‐2,3‐dimethoxy‐9,10‐dihydrochromeno[4,3‐b]pyrrolizin‐6 (8H)‐one, in particular, is a congener of the well‐known lamellarin G trimethyl ether. Preliminary results pertaining to an extension to chromenone‐fused indolizines are also reported.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
Chromenone‐Fused Pyrrolizines and Pyrrolizine Analogues of Lamellarins: Expanding the Lamellarin Family ; day:23 ; month:01 ; year:2024 ; extent:9
European journal of organic chemistry ; (23.01.2024) (gesamt 9)
- Urheber
-
Scalzullo, Stefania M.
Morgans, Garreth L.
Klintworth, Robin
de Koning, Charles B.
Fernandes, Manuel A.
Otterlo, Willem van
Michael, Joseph P.
- DOI
-
10.1002/ejoc.202301230
- URN
-
urn:nbn:de:101:1-2024012414253701939789
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
15.08.2025, 07:30 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Scalzullo, Stefania M.
- Morgans, Garreth L.
- Klintworth, Robin
- de Koning, Charles B.
- Fernandes, Manuel A.
- Otterlo, Willem van
- Michael, Joseph P.
Ähnliche Objekte (12)
Expanding the β ‐Lactamase Family in the Human Microbiome
Ring‐Expanding Rearrangement of Benzo‐Fused Tris‐Cycloheptenylenes towards Nonplanar Polycyclic Aromatic Hydrocarbons
cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin
Pleomorphic archaeal viruses: the family Pleolipoviridae is expanding by seven new species
Livres Analogues
Expanding of the Subject
Expanding the Romantic Circle
Height functions for motives, Hodge analogues, and Nevanlinna analogues
Expanding Role of Self Expanding Esophageal Stents
Mustard carbonate analogues
Expanding universe
Identification of a novel fused gene family implicates convergent evolution in eukaryotic calcium signaling
Expanding the β ‐Lactamase Family in the Human Microbiome
Ring‐Expanding Rearrangement of Benzo‐Fused Tris‐Cycloheptenylenes towards Nonplanar Polycyclic Aromatic Hydrocarbons
cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin
Pleomorphic archaeal viruses: the family Pleolipoviridae is expanding by seven new species
Livres Analogues
Expanding of the Subject
Expanding the Romantic Circle
Height functions for motives, Hodge analogues, and Nevanlinna analogues
Expanding Role of Self Expanding Esophageal Stents
Mustard carbonate analogues
Expanding universe
Identification of a novel fused gene family implicates convergent evolution in eukaryotic calcium signaling
Expanding the β ‐Lactamase Family in the Human Microbiome
Ring‐Expanding Rearrangement of Benzo‐Fused Tris‐Cycloheptenylenes towards Nonplanar Polycyclic Aromatic Hydrocarbons
cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin
Pleomorphic archaeal viruses: the family Pleolipoviridae is expanding by seven new species
Livres Analogues
Expanding of the Subject
Expanding the Romantic Circle
Height functions for motives, Hodge analogues, and Nevanlinna analogues
Expanding Role of Self Expanding Esophageal Stents
Mustard carbonate analogues
Expanding universe