Stable 5‐Substituted Cyclopentadienes for the Diels–Alder Cycloaddition and their Application to the Synthesis of Palau'amine

Hudon, Jonathan; Cernak, Timothy A.; Ashenhurst, James A.; Gleason, James L.

doi:10.1002/anie.200803344

Cited by 60 publications

(33 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For this reason and due to space limitations, only enantioselective routes to P-2-AIs will be described with the exception of the recent synthesis of racemic palau’amine by Baran. However mention must be made of outstanding contributions to this area by Overman, 49 Harran, 43 Horne, Ohta, 50 Carreira, 51 Chen, 52 and Lovely, 35,53 Gin, 54 Gleason, 55 and Williams. 56 …”

Section: Enantioselective Chemical Syntheses Of the Pyrrole-imidazomentioning

confidence: 99%

Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids

et al. 2011

View full text Add to dashboard Cite

The pyrrole-2-aminoimidazole (P-2-AI) alkaloids are a growing family of marine alkaloids, now numbering well over 150 members, with high topographical and biological information content. Their intriguing structural complexity, rich and compact stereochemical content, high N to C ratio (~1:2), and increasingly studied biological activities are attracting a growing number of researchers from numerous disciplines world-wide. This review surveys advances in this area with a focus on the structural diversity, biosynthetic hypotheses with increasing but still rare verifying experimental studies, asymmetric syntheses, and biological studies including cellular target receptor isolation studies of this stimulating and exciting alkaloid family.

show abstract

Section: Enantioselective Chemical Syntheses Of the Pyrrole-imidazomentioning

confidence: 99%

Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids

et al. 2011

View full text Add to dashboard Cite

show abstract

“…20 The Harran group has reported an oxidative enolate coupling/skeletal rearrangement approach to synthesize “axinellamines deficient in halogen”. 23 Additional synthetic approaches have been reported by the Austin, 22 Gin, 24 Gleason, 25 Williams, 26 Feldman, 27 and Nagasawa 28 groups.…”

Section: Total Synthesesmentioning

confidence: 99%

Dimeric pyrrole–imidazole alkaloids: synthetic approaches and biosynthetic hypotheses

Wang

et al. 2014

Chem. Commun.

View full text Add to dashboard Cite

The pyrrole-imidazole alkaloids are a group of structurally unique and biologically interesting marine sponge metabolites. Among them, the cyclic dimers have caught synthetic chemists’ attention particularly. Numerous synthetic strategies have been developed and various biosynthetic hypotheses have been proposed for these fascinating natural products. We discuss herein the synthetic approaches and the biosynthetic insights obtained from these studies.

show abstract

“…166,167 They also used a Diels-Alder/oxidative cleavage strategy to establish the key cyclopentyl ring of 1 ’. Although similar to the approach used by Carreira, the Gleason's approach allows for a more direct introduction of the requisite functionalities.…”

Section: The Higher Order Pyrrole-imidazole Alkaloidsmentioning

confidence: 99%

Syntheses of cyclic guanidine-containing natural products

Chen

2015

Tetrahedron

View full text Add to dashboard Cite

Naturally occurring guanidine derivatives frequently display medicinally useful properties. Among them, the higher order pyrrole-imidazole alkaloids, the dragmacidins, the crambescidins/batzelladines, and the saxitoxins/tetradotoxins have stimulated the development of many new synthetic methods over the past decades. We provide here an overview of the syntheses of these cyclic guanidine-containing natural products.

show abstract

Stable 5‐Substituted Cyclopentadienes for the Diels–Alder Cycloaddition and their Application to the Synthesis of Palau'amine

Cited by 60 publications

References 46 publications

Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids

Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids

Dimeric pyrrole–imidazole alkaloids: synthetic approaches and biosynthetic hypotheses

Syntheses of cyclic guanidine-containing natural products

Contact Info

Product

Resources

About