Synthesis of aspidodispermine via pericyclic framework reconstruction
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-B?cklund 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.
Reu?, Franziska,Heretsch, Philipp
p. 3956 - 3959
(2020/05/19)
Expedited Synthesis of Matrine Analogues through an Oxidative Cascade Addition/Double-Cyclization Radical Process
The addition of a nicotinate–xanthate derivative to N-allylindoles and N-allylpyrroles resulted in polycyclic heterocycle-fused pyridonaphthyridines through a tandem radical intermolecular/intramolecular oxidative addition reaction sequence that created three new C–C bonds and two new rings in a single event. Such polyheterocycles showcase the matrine alkaloid framework and are similar to indole–monoterpenoid natural products.
Olguín-Uribe, Simón,Mijangos, Marco V.,Amador-Sánchez, Yoarhy A.,Sánchez-Carmona, Miguel A.,Miranda, Luis D.
supporting information
p. 2481 - 2485
(2017/05/12)
Towards a new synthetic entry into the Iboga-alkaloid family
A novel retrosynthetic concept is presented that, in principle, allows access to many hitherto not accessible representatives of the Iboga-alkaloid family. The flexibility required by this approach is provided through a highly convergent assembly of the target, which allows for a control over the substitution pattern of the indole sub-system, as well as over the relative configuration of the aliphatic core of these alkaloids. The key step for the construction of the latter consists in an intramolecular nitrone-olehn 1,3-dipolar cycloaddition reaction of 26 to yield the crucial tricyclic isoxazolidine derivative 28.
Frauenfelder, Christine,Borschberg, Hans-Juerg
p. 1753 - 1765
(2007/10/03)
Tetrahydropyridines.
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Wenkert,Dave,Haglid,Lewis,Oishi,Stevens,Terashima
p. 747 - 753
(2007/10/04)
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