Short Synthetic Route Toward the Tricyclic Core of Schulzeines.

Kuntiyong, Punlop; Akkarasamiyo, Sunisa; Eksinitkun, Gedsirin

doi:10.1002/chin.200706202

Cited by 2 publications

(2 citation statements)

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“…In a model study toward the tricyclic core of schulzeines, Kuntiyong et al 87 synthesized a methoxy analogue 278 of the key tetrahydroisoquinoline fragment 265. Thus, acylation of 3,5dimethoxyphenylethylamine with benzyl L-glutamate led to the formation of amide 275.…”

Section: Pictet−spengler Cyclizationmentioning

confidence: 99%

Asymmetric Synthesis of Isoquinoline Alkaloids: 2004–2015

2016

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In the past decade, the asymmetric synthesis of chiral nonracemic isoquinoline alkaloids, a family of natural products showing a wide range of structural diversity and biological and pharmaceutical activity, has been based either on continuation or improvement of known traditional methods or on new, recently developed, strategies. Both diastereoselective and enantioselective catalytic methods have been applied. This review describes the stereochemically modified traditional syntheses (the Pictet-Spengler, the Bischler-Napieralski, and the Pomeranz-Fritsch-Bobbitt) along with strategies based on closing of the nitrogen-containing ring B of the isoquinoline core by the formation of bonds between C-N, N-C, C-N/N-C, and C-N/C-C atoms. Methods involving introduction of substituents at the C1 carbon of isoquinoline core along with syntheses applying various biocatalytic techniques have also been reviewed.

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Section: Pictet−spengler Cyclizationmentioning

confidence: 99%

Asymmetric Synthesis of Isoquinoline Alkaloids: 2004–2015

2016

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“…142−144 In an effort to synthesize the tricyclic core of the marine natural products referred to as schulzeines, the tricyclic scaffold of tetrahydroisoquinoline fused with δ-lactam 164 was synthesized from the hydroxylactam 163 in the presence of Lewis acid. 142 Hydroxylactam substrate 165, readily obtained from DIBAL-H reduction of the corresponding piperidine-2,6-dione substrate, was cyclized to the tricyclic compound 166 using TMSOTf as the acid to form NAIs in situ (Scheme 45). 143 Compound 166 was obtained as a mixture of two diastereomers and coupled to a C28 fatty-acid chain to yield marine natural products schulzeines B and C. 145 More quinolizinone scaffolds and some indolizinone scaffolds 168−172 were synthesized in moderate to high yields with poor diastereoselectivity from dibenzylamino-substituted hydroxylactams 167.…”

Section: Chemical Reviewsmentioning

confidence: 99%

Scaffold Diversity from N-Acyliminium Ions

Nielsen

2017

Chem. Rev.

167

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N-Acyliminium ions are powerful reactive species for the formation of carbon-carbon and carbon-heteroatom bonds. Strategies relying on intramolecular reactions of N-acyliminium intermediates, also referred to as N-acyliminium ion cyclization reactions, have been employed for the construction of structurally diverse scaffolds, ranging from simple bicyclic skeletons to complex polycyclic systems and natural-product-like compounds. This review aims to provide an overview of cyclization reactions of N-acyliminium ions derived from various precursors for the assembly of structurally diverse scaffolds, covering the literature over the past 12 years (from 2004 to 2015).

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Short Synthetic Route Toward the Tricyclic Core of Schulzeines.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 2 publications

References 1 publication

Asymmetric Synthesis of Isoquinoline Alkaloids: 2004–2015

Asymmetric Synthesis of Isoquinoline Alkaloids: 2004–2015

Scaffold Diversity from N-Acyliminium Ions

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