Enyne and dienyne metathesis reactions in β-carbolines

González-Gómez, Álvaro; Domı́nguez, Gema; Castells, Javier Pérez

doi:10.1016/j.tetlet.2005.07.140

Cited by 28 publications

(9 citation statements)

References 21 publications

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“…Ruthenium-catalyzed RCM of 1,7-, 1,8-, and 1,9-enynes were described [1257][1258][1259][1260]. A mechanism involving an ene-thenyne metathesis of tethered enynes was supported by labeling experiments [1261].…”

Section: Metathesis Reactionsmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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Section: Metathesis Reactionsmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…[41] As an example, Scheme 25 shows the construction of the bridged THBC 30 characterized by an enyne ring-closing metathesis of 29. Scheme 25. We [42] and others [43] have shown that enynes and dienynes based on the β-carboline system give metathesis productsin particular, five-to seven-membered rings fused with the β-carboline -in the presence of ruthenium catalysts. Scheme 26 shows an enyne-RCM in which a five-membered ring is formed.…”

Section: Further Cyclizationsmentioning

confidence: 94%

Chemistry of β‐Carbolines as Synthetic Intermediates

Domı́nguez

Pérez‐Castells

2011

Eur J Org Chem

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Abstractβ‐Carbolines are present in a wide variety of indole alkaloids that display important biological activities. Here we review the most recent aspects of the chemistry of β‐carbolines with a focus on functionalization of the β‐carboline system and transformations into other interesting compounds. Aromatizations, reductions and alkylations of the heterocyclic system are thus summarized first, followed by methodologies directed towards the formation of additional fused rings. Finally, rearrangements that transform β‐carbolines into other heterocyclic systems are covered.

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“…Castells and co-workers also presented an example of a tandem enyne RCM/oxidation sequence. [104] β-Carbolinebased dienyne 263 was treated with the GH-II catalyst in toluene at reflux to yield a new pentacyclic compound 264, which was assumed to be generated from the dienyne metathesis product by spontaneous oxidation (Scheme 65). Nay and co-workers observed a similar oxidation pathway following the RCM of allylic propargylic ether 265, generating furan 267 from its precursor 266 (Scheme 65).…”

Section: Tandem Enyne Metathesis/oxidationmentioning

confidence: 99%