Total Synthesis of (+)-Panacene

Alnafta, Neanne; Schmidt, Johannes; Nesbitt, Caroline L.; McErlean, Christopher S. P.

doi:10.1021/acs.orglett.6b03219

Cited by 19 publications

(10 citation statements)

References 33 publications

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“…Although allene is found in a number (∼160) of natural products, like cepacin, puna’auic acid, panacene, etc . , the existence of an allene group in the superfamily of macrolide was unprecedented.…”

supporting

confidence: 56%

Combining NMR-Based Metabolic Profiling and Genome Mining for the Accelerated Discovery of Archangiumide, an Allenic Macrolide from the Myxobacterium Archangium violaceum SDU8

Wang

et al. 2021

Org. Lett.

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An unprecedented 19-membered allenic macrolide archangiumide (1) was discovered from the myxobacterium Archangium violaceum SDU8 by integrating NMR-based metabolic profiling and genome mining. Its biosynthesis pathway was proposed based on the architectural analysis of the encoding trans-AT PKS genes and validated by isotope labeling. The methodology of combing 2D NMR-based metabolic profiling and bioinformatics-aided structure prediction, as exemplified by this study, is anticipated to improve discovery efficiency of a broader range of microbial “dark matter”.

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supporting

confidence: 56%

Combining NMR-Based Metabolic Profiling and Genome Mining for the Accelerated Discovery of Archangiumide, an Allenic Macrolide from the Myxobacterium Archangium violaceum SDU8

Wang

et al. 2021

Org. Lett.

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“…In a beautiful exposition of the utility of total synthesis, the putative linear contiguous polyketide precursor of the mollusc metabolite dolabriferol has been shown to undergo regioselective retro-Claisen fragmentation to form the natural product under mild conditions. 679 Total syntheses of (+)-panacene, 680 brominated chamigrene sesquiterpenes, including aplydactone, 681,682 the protein synthesis inhibitor chlorolissoclimide, 683 and (À)-chromodorolide B 684 have been reported. Carotenoid mytiloxanthin, originally reported from the sea mussel Mytilus californianus, quenches singlet oxygen and inhibits lipid peroxidation.…”

Section: Molluscsmentioning

confidence: 99%

Marine natural products

et al. 2018

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Covering: 2016. Previous review: Nat. Prod. Rep., 2017, 34, 235-294This review covers the literature published in 2016 for marine natural products (MNPs), with 757 citations (643 for the period January to December 2016) 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 (1277 in 432 papers for 2016), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that led to the revision of structures or stereochemistries, have been included.

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“…In 2016, McErlean and co-workers accomplished the first total synthesis of the natural marine product (+)-panacene in 17% overall yield (Scheme 24). 37 The racemic 3-oxo-2,3-dihydrobenzofuran-2-acetate was subjected to ATH/DKR using (S,S)-CAT13 in DMF in the presence of HCO 2 H as the hydrogen source and i-Pr 2 NEt as a base to furnish the desired enantioenriched tricyclic lactone in 78% yield with 73% ee, which could be upgraded to 96% after recrystallization. This spontaneous lactonization enabled efficient generation of the tricyclic core of (+)-panacene.…”

Section: Scheme 23mentioning

confidence: 99%

Recent Progress and Applications of Transition-Metal-Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution

et al. 2020

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Based on the ever-increasing demand for enantiomerically pure compounds, the development of efficient, atom-economical, and sustainable methods to produce chiral alcohols and amines is a major concern. Homogeneous asymmetric catalysis with transition-metal complexes including asymmetric hydrogenation (AH) and transfer hydrogenation (ATH) of ketones and imines through dynamic kinetic resolution (DKR) allowing the construction of up to three stereogenic centers is the main focus of the present short review, emphasizing the development of new catalytic systems combined to new classes of substrates and their applications as well.1 Introduction2 Asymmetric Hydrogenation via Dynamic Kinetic Resolution2.1 α-Substituted Ketones2.2 α-Substituted β-Keto Esters and Amides2.3 α-Substituted Esters2.4 Imine Derivatives3 Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution3.1 α-Substituted Ketones3.2 α-Substituted β-Keto Esters, Amides, and Sulfonamides3.3 α,β-Disubstituted Cyclic Ketones3.4 β-Substituted Ketones3.5 Imine Derivatives4. Conclusion

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Total Synthesis of (+)-Panacene

Cited by 19 publications

References 33 publications

Combining NMR-Based Metabolic Profiling and Genome Mining for the Accelerated Discovery of Archangiumide, an Allenic Macrolide from the Myxobacterium Archangium violaceum SDU8

Combining NMR-Based Metabolic Profiling and Genome Mining for the Accelerated Discovery of Archangiumide, an Allenic Macrolide from the Myxobacterium Archangium violaceum SDU8

Marine natural products

Recent Progress and Applications of Transition-Metal-Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution

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