Total Synthesis of Aspeverin via an Iodine(III)-Mediated Oxidative Cyclization

Levinson, Adam M.

doi:10.1021/ol5024163

Cited by 24 publications

(17 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…306,307 (AE)-sorbiterrin A 308 (Penicillium terrestre), 309 (À)-auronamide C 310 (Penicillium aurantiogriseum), 311 calcaripeptides A-C 312 (Calcarisporium sp. ), 313 (À)-aspergilazine A 314 (Aspergillus taichungensis), 315 aspirin 316 (Aspergillus versicolor), 317 cochliomycin B 318 (Cochliobolus lunatus), 319 dendroides 320 (Dendrodochium sp.) A, 321 B 322 and E, 322 paecilocin 323 (Paecilomyces variotii), 324 penicimonoterpene 325 (Penicillium chrysogenum) 326 and (+)-penostatin E 327 (Penicillium sp.).…”

Section: Marine-sourced Fungi (Excluding From Mangroves)mentioning

confidence: 99%

Marine natural products

et al. 2016

View full text Add to dashboard Cite

This review covers the literature published in 2014 for marine natural products (MNPs), with 1116 citations (753 for the period January to December 2014) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1378 in 456 papers for 2014), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

show abstract

Section: Marine-sourced Fungi (Excluding From Mangroves)mentioning

confidence: 99%

Marine natural products

et al. 2016

View full text Add to dashboard Cite

show abstract

“…Aspeverin ( 192 ), a prenylated indole alkaloid, was synthesized using the Curtius rearrangement as a key step. 121 The bicyclic urethane linkage functionality is distinctive of this class of natural products. To this aim ester 189 was converted into the corresponding acyl azide 190 .…”

Section: Application Of the Curtius Rearrangement In Total Synthesismentioning

confidence: 99%

The Curtius rearrangement: mechanistic insight and recent applications in natural product syntheses

2018

View full text Add to dashboard Cite

The Curtius rearrangement is a versatile reaction in which a carboxylic acid can be converted to an isocyanate through an acyl azide intermediate under mild conditions. The resulting stable isocyanate can then be readily transformed into a variety of amines and amine derivatives including urethanes and ureas. There have been wide-ranging applications of the Curtius rearrangement in the synthesis of natural products and their derivatives. Also, this reaction has been extensively utilized in the synthesis and application of a variety of biomolecules. In this review, we present mechanistic studies, chemical methodologies and reagents for the synthesis of isocyanates from carboxylic acids, the conversion of isocyanates to amines and amine derivatives, and their applications in the synthesis of bioactive natural products and their congeners.

show abstract

“…It showed inhibitory activity against marine phytoplankton ( Heterosigma akashiwo ) with the EC 50 values of 16.7 and 9.0 μM for 24 and 96 h, respectively. The structure of compound 115 containing an unprecedented cyclic carbamate linkage and a rare cyano could be assembled through a dipeptide-like precursor with dimethylallyl pyrophosphate (DMAPP) [ 147 , 148 ], and has promoted the attention of chemists from a totally synthetic perspective [ 149 ]. Varioxepine A ( 116 , Figure 19 ), a 3 H -oxepine-containing alkaloid with an unprecedented oxa-cage unit, was isolated from Paecilomyces variotii , an endophytic fungus residing in marine red alga [ 150 ].…”

Section: Hybrid Productsmentioning

confidence: 99%

Structural Diversity and Biological Activities of Novel Secondary Metabolites from Endophytes

Han

Lou

2018

Molecules

View full text Add to dashboard Cite

Exploration of structurally novel natural products greatly facilitates the discovery of biologically active pharmacophores that are biologically validated starting points for the development of new drugs. Endophytes that colonize the internal tissues of plant species, have been proven to produce a large number of structurally diverse secondary metabolites. These molecules exhibit remarkable biological activities, including antimicrobial, anticancer, anti-inflammatory and antiviral properties, to name but a few. This review surveys the structurally diverse natural products with new carbon skeletons, unusual ring systems, or rare structural moieties that have been isolated from endophytes between 1996 and 2016. It covers their structures and bioactivities. Biosynthesis and/or total syntheses of some important compounds are also highlighted. Some novel secondary metabolites with marked biological activities might deserve more attention from chemists and biologists in further studies.

show abstract

Total Synthesis of Aspeverin via an Iodine(III)-Mediated Oxidative Cyclization

Cited by 24 publications

References 55 publications

Marine natural products

Marine natural products

The Curtius rearrangement: mechanistic insight and recent applications in natural product syntheses

Structural Diversity and Biological Activities of Novel Secondary Metabolites from Endophytes

Contact Info

Product

Resources

About