#totalsynthesis — Public Fediverse posts
Live and recent posts from across the Fediverse tagged #totalsynthesis, aggregated by home.social.
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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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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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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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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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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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⚗️ 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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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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⚗️ #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 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.
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Stephadiamine is a popular synthetic challenge which resulted in many total syntheses before. Now, Jieping Zhu (EPFL, Lausanne) and co-workers were able to report in #JACS a new route to the #alkaloid with a hasubanan core structure featuring a diastereoselective intramolecular dipolar cycloaddition.
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Although the first total synthesis of taxol was accomplished nearly 30 years ago, its complex structure still motivates researchers to invent new synthetic routes. Now, Masayuki Inoue and co-workers (University of #Tokyo #Japan) published a radical-based approach to the #polyketide in the journal #AngewandteChemie
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Synthesis of prorocentin by Alois Fürstner and co-workers from MPI Mülheim a.d. Ruhr @maxplanckgesellschaft published in #JACS is a showcase of why total synthesis is still needed: Determination of the absolute configuration and structural revision was only possible after extensive synthetic efforts.
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Total synthesis of Alterbrassicene C:
John L Wood (Baylor University, #US) et al reported the first total synthesis of the terpenoid in #JACS (10.1021/jacs.2c12275). I feautered this #synthesis because I like these kinds of oxa-Michael cascade reactions. Since many terpenoid syntheses these days often involve CH activation strategies, it's refreshing to see other approaches in action.
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Total synthesis of periglaucine C and other hasubanan alkaloids. The Shuanhu Gao Group from the East China Normal University (Shanghai) published in the journal Angewandte Chemie the synthesis of these natural products featuring an intramolecular Diels Alder reaction after photoenolization and a late stage Michael addition.
https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.202214873