Journal ArticleDOI
Deconjugation of α,β-unsaturated esters and an intramolecular Michael reaction of bis-α,β-unsaturated esters with trialkylsilyl trifluoromethanesulfonate in the presence of tertiary amine: synthesis of (±)-ricciocarpin A
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TLDR
In this paper, a trialkylsilyl trifluoromethansulfonate was used to produce cyclopentanes 14a and 20a and cyclohexanes 14b and 20b.Abstract:
Treatment of the α,β-unsaturated esters 1, 6 and 8 with trialkylsilyl trifluoromethanesulfonate in the presence of a tertiary amine gave, via silyl dienol ethers, the corresponding deconjugated esters 3, 7 and 9 as the major products, respectively. Reaction of bis-α,β-unsaturated esters 12a and 12b with a trialkylsilyl trifluoromethansulfonate in the presence of a tertiary amine caused an intramolecular Michael reaction to produce the cyclopentanes 14a and 20a and the cyclohexanes 14b and 20b. Bicyclic compounds 21a and 21b formed by tandem Michael–Dieckmann or intramolecular Diels–Alder reaction were concurrently obtained. The cyclohexane derivative 14b was converted into the racemate of a sesquiterpene, (±)-ricciocarpin A 22.read more
Citations
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Journal ArticleDOI
Iterative Design and Optimization of Initially Inactive Proteolysis Targeting Chimeras (PROTACs) Identify VZ185 as a Potent, Fast, and Selective von Hippel–Lindau (VHL) Based Dual Degrader Probe of BRD9 and BRD7
Vittoria Zoppi,Vittoria Zoppi,Scott J. Hughes,Chiara Maniaci,Andrea Testa,Teresa Gmaschitz,Corinna Wieshofer,Manfred Koegl,Kristin M. Riching,Danette L. Daniels,Andrea Spallarossa,Alessio Ciulli +11 more
TL;DR: This work describes a probe-quality degrader for a ligase–target pair deemed unsuitable: the von Hippel–Lindau (VHL) and BRD9, a bromodomain-containing subunit of the SWI/SNF chromatin remodeling complex BAF.
Journal ArticleDOI
Total synthesis of dysidiolide
E. J. Corey and,Bryan E. Roberts +1 more
TL;DR: The cdc25A protein phosphatase inhibitor dysidiolide has been synthesized enantioselectively, starting from the enantiomerically pure ketal enone 2 and using a cationic rearrangement as the key step to produce the fully substituted bicyclic core of the natural product.
Journal ArticleDOI
Concise synthesis of ricciocarpin A and discovery of a more potent analogue
Anna Michrowska,Benjamin List +1 more
TL;DR: The key feature of the synthesis is a one-pot, three-step, organocatalytic reductive Michael-Tishchenko cascade that resulted in the synthesis of the natural product, but also of its antipode and four other structural analogues.
Journal ArticleDOI
Total Synthesis of Cyanolide A in the Absence of Protecting Groups, Chiral Auxiliaries, or Premetalated Carbon Nucleophiles
TL;DR: A total synthesis of cyanolide A is reported in the absence of protecting groups, chiral auxiliaries, or premetalated C-nucleophiles in fewer than half the steps of any previous approach.
References
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Journal ArticleDOI
Bryophytes, a Source of Biologically Active, Naturally Occurring Material?
TL;DR: In this article, the plant category of mosses (bryophytes) were neglected for a long time and they have now been shown to be a storehouse of naturally occurring materials, including some with novel chemical structures.
Journal ArticleDOI
Trialkylsilyl Perfluoroalkanesulfonates: Highly Reactive Silylating Agents and Lewis Acids in Organic Synthesis
Herbert Emde,Dietmar Domsch,Harry Feger,Ulrich Frick,Andreas Götz,Hans Herbert Hergott,Karin Hofmann,Wolfgang Kober,Konrad Krägeloh,Thomas Oesterle,Wolfgang Steppan,Waldemar West,Gerhard Simchen +12 more
Book ChapterDOI
Formation of Enolates
TL;DR: The stereochemical outcome of an enolate reaction often depends on the geometry of the enolate and therefore the selective formation of enolates is a key step in many bond-forming processes as mentioned in this paper.