Syntheses of cyclic guanidine-containing natural products

Ma, Yuyong; De, Saptarshi; Chen, Chuo

doi:10.1016/j.tet.2014.11.056

Cited by 60 publications

(30 citation statements)

References 423 publications

(331 reference statements)

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“…Several members of the batzelladine, crambescidin, and ptilomycalin families have been accessed through total synthesis. 8,10 The challenges faced in all of the approaches to this class of natural products have highlighted the many difficulties associated with the synthesis of charged and densely functionalized structures in an asymmetric fashion. These efforts have provided the first synthetic access to this class of natural products and in some limited studies the material obtained through synthesis has provided insight into the biological potential offered by these alkaloids.…”

Section: An Overview Of Synthetic Approachesmentioning

confidence: 99%

“…8–10 The first member of this class to be reported, ptilomycalin A ( 6 , Fig. 2), was isolated from the Caribbean sponge Ptilocaulis spiculijer and from the Red Sea sponge Hemimycale sp.…”

Section: Introductionmentioning

confidence: 99%

“…8– 10 The guanidinium core 5 is shared among the majority of the members of this class with a few exceptions.…”

Section: Introductionmentioning

confidence: 99%

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Structure, synthesis and biological properties of the pentacyclic guanidinium alkaloids

Shi

Moazami

Pierce

2017

Bioorganic & Medicinal Chemistry

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The pentacyclic guanidinium alkaloids (PGAs) are a family of marine natural products that possess a poly-cyclic guanidine-containing core and a long alkyl chain tethered spermidine-derived tail that is rarely observed in other natural products. These natural products exhibit potent activities on a wide range of organisms and therefore have attracted the attention of many synthetic chemists; however, the structure-activity relationships and mechanisms of action of PGAs remain largely elusive. Herein we summarize the structure, synthesis, toxicity and mechanisms of action of PGAs and highlight their potential as chemical probes and/or therapeutic leads.

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Section: An Overview Of Synthetic Approachesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Structure, synthesis and biological properties of the pentacyclic guanidinium alkaloids

Shi

Moazami

Pierce

2017

Bioorganic & Medicinal Chemistry

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“…As part of the amino acid arginine, they play an important role in biochemistry, mainly by forming ion pairs. In addition, numerous guanidine derivatives with complex cyclic structures can be found in natural products [1]. Simple guanidines such as tetramethylguanidine have been used as strong Brønsted bases in countless applications [2–3].…”

Section: Introductionmentioning

confidence: 99%

A chiral analog of the bicyclic guanidine TBD: synthesis, structure and Brønsted base catalysis

Goldberg¹,

Sartakov²,

Bats³

et al. 2016

Beilstein J. Org. Chem.

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SummaryStarting from (S)-β-phenylalanine, easily accessible by lipase-catalyzed kinetic resolution, a chiral triamine was assembled by a reductive amination and finally cyclized to form the title compound 10. In the crystals of the guanidinium benzoate salt the six membered rings of 10 adopt conformations close to an envelope with the phenyl substituents in pseudo-axial positions. The unprotonated guanidine 10 catalyzes Diels–Alder reactions of anthrones and maleimides (25–30% ee). It also promotes as a strong Brønsted base the retro-aldol reaction of some cycloadducts with kinetic resolution of the enantiomers. In three cases, the retro-aldol products (48–83% ee) could be recrystallized to high enantiopurity (≥95% ee). The absolute configuration of several compounds is supported by anomalous X-ray diffraction and by chemical correlation.

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“…6 Our lab has pursued an approach to this group of alkaloids based on a Diels-Alder 7 /rearrangement 8 strategy as a means to access the spiro fused EF-rings. 9 Part of the motivation behind this strategy derived from the ability to use the known stereochemical characteristics of the Diels-Alder (DA) reaction as a means to establish the stereochemical relationships in the E-ring.…”

mentioning

confidence: 99%

Preparation and Diels–Alder reactions of 1′-heterosubsituted vinylimidazoles

Ray

Mukherjee

Das

et al. 2015

Tetrahedron Letters

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A Diels-Alder/rearrangement sequence has been pursued in our lab en route to a number of oroidin dimers. In order to access the fully substituted core of these molecules, 1′,2′-disubstituted 4-vinylimidazoles were required as dienes. The preparation of a series of a 4-vinylimidazoles containing substituents on the vinyl moiety via hydroalumination/electrophilic trapping or hydrosilylation are described. These derivatives undergo Diels-Alder reactions with N-phenylmaleimide to provide the tetrahydrobenzimidazole derivatives. The cycloadducts derived from halosubstituted systems generally undergo elimination, leading to the corresponding dihydrobenzimidazole, whereas the silyl and stannyl derivatives provide the corresponding 4-substituted tetrahydrobenzimidazole.

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Syntheses of cyclic guanidine-containing natural products

Cited by 60 publications

References 423 publications

Structure, synthesis and biological properties of the pentacyclic guanidinium alkaloids

Structure, synthesis and biological properties of the pentacyclic guanidinium alkaloids

A chiral analog of the bicyclic guanidine TBD: synthesis, structure and Brønsted base catalysis

Preparation and Diels–Alder reactions of 1′-heterosubsituted vinylimidazoles

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