#totalsynthesis — Public Fediverse posts
Live and recent posts from across the Fediverse tagged #totalsynthesis, aggregated by home.social.
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🎁 Happy 80th birthday to K. C. Nicolaou—master of “the art of total synthesis”, whose landmark syntheses of Calicheamicin, Taxol, Brevetoxin B, Epothilone, and Vancomycin helped shape modern organic chemistry. #TotalSynthesis #OrganicChemistry
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Novel enantioselective #synthesis of rubriflordilactone B by Gui and colleagues from the Chinese Academy of Science published in #JACS
This is already the second total synthesis of this group, with an interesting reaction cascade as the key reaction in this process. -
Joseph Tuccinardi and John Wood from Baylor University (#USA), introduced a novel strategy to efficiently synthesize the core scaffold of aleutianamine. Their study involved a vinylogous Mukaiyama-Michael reaction cascade using two previously unknown coupling partners. Published in #JACS
https://me.organicchemistry.eu/post/aleutianamine-jacs-2025/
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Computer-aided synthesis: R. Shenvi and C. Li published in #Nature the total synthesis of 25 picrotoxanes. Their 1,5-HAT key reaction was challenged by β-scission, therefore DFT based calculations helped to design usable intermediates.
Read more on my page: https://me.organicchemistry.eu/post/picrotoxanes-nature-2024/
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Total Synthesis of Kasugamycin:
Aminoglycoside antibiotic prepared from naturally derived carbohydrates
https://www.chemistryviews.org/total-synthesis-of-kasugamycin/#orgchem #glycosides #totalsynthesis #chemistry #chemistryviews #chemviews
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Total Synthesis of (+)-Mannolide B
Path to a natural product with a complex, fused hexacyclic scaffold
https://www.chemistryviews.org/total-synthesis-of-mannolide-b/
#totalsynthesis #naturalproducts #chemistry #chemistryviews #chemviews
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Another total synthesis in the spotlight: Already early this year Mingji Dai and his research team described the total synthesis of heilonine in #JACS (doi: 10.1021/jacs.3c13492). This synthesis is short and elegant, using multiple C-H functionalisations and a Nazarov cyclisation for their key step.
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Total Synthesis of Pleurotin (JACS Au, Y. Q. Long 2024)
Pleurotin is a benzoquinone meroterpenoid that was first isolated in the late 1940s. Since that time, several total syntheses of this compound have been reported. Recently, Ya-Qiu Long and his team from Soochow University (#China) published a novel synthetic route in the journal JACS Au.
Read more here: https://www.organicchemistry.eu/books/total-syntheses-of-natural-products/page/total-synthesis-of-pleurotin-y-q-long-2024
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First Total Synthesis of Garajonone
Two-stage synthetic strategy provides access to ryanodane diterpenes, a type of structurally complex natural product
https://www.chemistryviews.org/first-total-synthesis-of-garajonone/
#naturalproducts #totalsynthesis #chemistry #chemistryviews #chemviews
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Stasseriolides are a class of polyketide natural products with interesting biological activities, but they are limited in natural abundance. A recent synthesis of stasseriolides A-D by Alois Fürstner's group at the Max Planck Institute für Kohlenforschung reported in Angewandte Chemie employed ring-closing alkyne metathesis, providing access to the natural products and enabling the preparation of analogues.
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Terpenoids are a large class of secondary #NaturalProducts, with some possessing an interesting polycyclic core that has attracted research interest. Researchers from #Shandong #University in #China led by Ze-Jun Xu (徐泽军) and Hong-Xiang Luo (娄红祥) have now reported the #TotalSynthesis of platensilin and platensimycin, as well as the formal synthesis of platencin, using a biomimetic approach from a common precursor.
Read more in #JACS: https://pubs.acs.org/doi/10.1021/jacs.4c02256
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Solvent-Promoted Total Syntheses of Sesquiterpenoid Dimers
Gochnatiolide D and ainsliadimer A prepared via a one-pot sequence using hexafluoroisopropanol (HFIP) as the solvent
https://www.chemistryviews.org/solvent-promoted-total-syntheses-of-sesquiterpenoid-dimers/
#totalsynthesis #hfip #sesquiterpenoids #orgchem #chemistry #chemistryviews
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Total Synthesis of (+)-Lemnardosinane A
A sesquiterpenoid natural product isolated from marine soft corals
https://www.chemistryviews.org/total-synthesis-of-lemnardosinane-a/
#totalsynthesis #organicchemistry #orgchem #chemistry #chemistryviews
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My Reading Tip of the Week:
Scabrolide A, a polycyclic marine natural product, has fascinated chemists due to its highly constrained structure. Recently, Pengfei Hu and colleagues from Westlake University in Hangzhou, China, published an innovative radical cascade strategy for efficiently synthesizing the scaffold of this polycyclic compound.
Divergent Synthesis of Scabrolide A and Havellockate via an exo-exo-endo Radical Cascade
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Researchers (Rahul Choudhury et al.) from the Academy of Scientific and Innovative Research in #India reported in the journal #OrganicLetters the total synthesis of benzo[g]isochromene stereodiads. Their synthesis using a TiCl4 promoted #Aldol coupling showed that the previously reported absolute structure did not agree with the structure of the natural product and a revision was suggested.
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Melognine was thought to be a highly complex alkaloid with a polycyclic ring system. Yui Irie and Satoshi Yokoshima (Nagoya University, #Japan) published a total synthesis of the proposed structure in the journal #JACS. However, the synthesised structure turned out to have different analytical properties. The authors concluded that melognine is actually identical to melodinine L. Check out the intriguing total synthesis route on JACS:
https://pubs.acs.org/doi/10.1021/jacs.4c02086 -
If you have some time, take a look at the total synthesis of Hunterine A by Elliot Hicks, Kengo Inoue and Brian Stoltz published in #JACS (#OpenAccess). Very elegant synthesis and late-stage cyclization strategy.
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First Total Synthesis of Pepluacetal
Route relying on a Wolff rearrangement/lactonization cascade, a ring-closing metathesis/cyclopropanation sequence, and a late-stage transannular carbenoid insertionhttps://www.chemistryviews.org/first-total-synthesis-of-pepluacetal/
@angew_chem #chemistry #chemistryviews #chemviews #chemivers #Research #TotalSynthesis #organicchemistry #angewandtechemie
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Paper out! Only 7.5 years after defending my theses. Finally I can close that chapter of my life.
https://onlinelibrary.wiley.com/doi/10.1002/anie.202315423
#TotalSynthesis #naturalproducts -
⚗️ Using the Bunsen burner for the final step of a complex total synthesis?
📰 #OpenAccess #TotalSynthesis of Euphorikanin A by Erick Carreira and colleagues from #ETH Zurich (#Switzerland) published in #JACS. A late-stage atrospecific cascade reaction led to the core structure of the terpene and pyrrolysis finally yielded the natural product.
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First Total Syntheses of Hyperireflexolides A and B: Bioinspired pathway involves dearomatization and fragmentation of an acylphloroglucinol
#chemistry #chemistryviews #chemviews #chemiverse #totalsynthesis #organicchemistry #research
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📰 Total synthesis of kratom pseudoindoxyl metabolite by Tibor Soós and co-workers (Research Center for Natural Sciences #Hungary) showed rapid isomerization of this natural product in protic solvents. The synthesis published in #AngewandteChemie provided multigram amounts of this alkaloid and can be used for the synthesis of analogues.
https://onlinelibrary.wiley.com/doi/10.1002/anie.202303700
#Chemistry #TotalSynthesis #OrganicChemistry #Research #Science
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The #TotalSynthesis of highly condensed polycyclic terpenoids has been a hot topic in #Chemistry recently. Yandong Zhang (#Xiamen University, #China) and co-workers now were able to synthesize such complex terpenes by epoxide-ene cyclization, oxygenation, and subsequent skeletal rearrangement. Read more about this protecting group free total synthesis in #JACS: https://pubs.acs.org/doi/10.1021/jacs.3c06442
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Synthesis of highly complex terpenoids reported by Shuanhu Gao and co-workers from the East China Normal #University (#Shanghai #China). Cephinoid P and other related terpenoids were accessible by Nicholas/Hosomi-Sakurai cascade reaction and Pauson-Khand reaction. Published in #JACS
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Total Synthesis of Mindapyrroles A and B: Investigation of the antibacterial activity and the mechanism of action of two natural products
#chemistry #chemistryviews #chemviews # chemiverse #Research #totalsynthesis #organicchemistry #chemcon
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First Total Synthesis of Thiamyxins A–C and E: Potent class of RNA-virus-inhibiting (cyclo)depsipeptides
#chemistry #chemistryviews #chemviews #research #chemiverse #chemcon #totalsynthesis #virus
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Total Synthesis of Chaetoglobin A: Dimeric alkaloid from a fungus has a chiral axis connecting two azaphilone systems
#chemistry #chemistryviews #chemviews #scicon #chemivere #research #totalsynthesis #organicsynthesis #lab #science
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⚗️ #TotalSynthesis of Waixenicin A, 9-Deacetoxy-14,15-deepoxyxeniculin and Xeniafaraunol A by Thomas Magauer and colleagues (#University of #Innsbruck @uniinnsbruck #Austria) published recently in #JACS featuring an unusual alkylation ring closing strategy.
#chemistry #organicchemistry @chemistry
📰 https://pubs.acs.org/doi/10.1021/jacs.3c03366 -
The total synthesis of lucidumone, a ganoderma meroterpenoid, has been achieved by a team led by Hisanaka Ito from the #Tokyo University of Pharmacy and Life Sciences in #Japan and published in #AngewandteChemie. The synthesis involved a 10-step sequence, which included a one-pot preparation of the tetracyclic core skeleton via Claisen rearrangement and intramolecular aldol reaction.
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The beauty of spirocyclic compounds: Total synthesis of illisimonin A by Markus Kalesse and co-workers from the University Hannover published recently in #JACS
Nazarov/ene cyclization lead to key intermediate for the #synthesis of this terpenoid.