ChemInform Abstract: Total Syntheses of (-)-Macrolactin A, (+)-Macrolactin E, and (-)-Macrolactinic Acid: An Exercise in Stille Cross-Coupling Chemistry.

ChemInform ◽  
2010 ◽  
Vol 29 (33) ◽  
pp. no-no
Author(s):  
A. B. III SMITH ◽  
G. R. OTT
Keyword(s):  
Cross Coupling ◽  
Total Syntheses ◽  
Macrolactin A

Formal Total Syntheses of Crocacin A-D

2005 ◽  
Vol 70 (10) ◽  
pp. 1696-1708 ◽  
Author(s):  
Magnus Besev ◽  
Christof Brehm ◽  
Alois Fürstner
Keyword(s):  
Natural Products ◽  
Aldol Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
The Common ◽  
Selective Addition

A concise route to the common polyketide fragment5of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features asyn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzedanti-selective addition of propargyl mesylate10to the chiral aldehyde9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.

Rapid Formation of Advanced Scaffolds from Phenols and Anilines

Synlett ◽  
2018 ◽  
Vol 30 (06) ◽  
pp. 647-664
Author(s):  
Sylvain Canesi
Keyword(s):  
Total Synthesis ◽  
Cross Coupling ◽  
Protecting Groups ◽  
Complex Structures ◽  
Protecting Group ◽  
Total Syntheses ◽  
Aniline Derivatives ◽  
Pinacol Rearrangement ◽  
Rapid Formation ◽  
Aromatic Systems

This article is an account of our efforts over the last decade to functionalize phenols and anilines at any position and to use these compounds to generate substituted aromatic systems and advanced unsaturated cyclohexanone moieties, enabling the rapid formation of complex structures. Total syntheses of numerous natural products involving such intermediates were achieved.1 Introduction2 ortho-Functionalization of Phenols and Aniline Derivatives Mediated by Iodanes (III) and Synthesis of Panacene2.1 Cross-Coupling with Aniline Derivatives2.2 Dearomative Cycloaddition of Arenes and Heteroarenes2.3 Total Synthesis of Panacene3 meta-Functionalization of Aniline Derivatives and Synthesis of Erysotramidine3.1 meta-Functionalization of Aniline Derivatives3.2 Total Synthesis of Erysotramidine4 para-Functionalization of Phenols and Applications in Total Synthesis4.1 Bimolecular Approach Mediated by Protecting Groups4.2 ipso-Rearrangement4.3 Oxidative Alkyl Shift4.4 Oxidative Prins-Pinacol Rearrangement4.5 Oxidative Prins-Type Reaction4.6 Total Synthesis of (–)-Fortucine4.7 Total Synthesis of Isostrychnine4.8 Total Synthesis of (–)-Strychnopivotine5 Development of a Functional Protecting Group

Iron Catalysis in Target Synthesis

Synthesis ◽  
2020 ◽  
Vol 52 (07) ◽  
pp. 949-963
Author(s):  
Peter DaBell ◽  
Stephen P. Thomas
Keyword(s):  
Natural Products ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Organic Transformations ◽  
Total Syntheses ◽  
Iron Catalysis ◽  
Cross Coupling Reactions ◽  
Target Synthesis

The use of iron-catalysed organic transformations in the total syntheses of natural products has increased significantly. Iron-catalysed cross-coupling reactions are now widely applied in total syntheses and many other transformations, such as alkene functionalisation, oxidation, and cyclisation. The development of these processes, as well as many examples of their use in target synthesis, is presented here.1 Introduction2 Cross-Coupling Reactions3 Functionalisation of Unactivated Alkenes4 Carbocyclisation Reactions5 Oxidations6 Further Examples7 Conclusions

scholarly journals Tris(acetylacetonato) Iron(III): Recent Developments and Synthetic Applications

Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 161-177 ◽  
Author(s):  
Dennis Lübken ◽  
Marius Saxarra ◽  
Markus Kalesse
Keyword(s):  
Hydrogen Atom ◽  
Natural Product ◽  
Cross Coupling ◽  
Short Review ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Cross Coupling Reactions ◽  
Recent Developments

Tris(acetylacetonato) iron(III) [Fe(acac)3] is an indispensable reagent in synthetic chemistry. Its applications range from hydrogen atom transfer to cross-coupling reactions and to use as a Lewis acid. Consequently, the exceptional utility of Fe(acac)3 has been demonstrated in several total syntheses. This short review summarizes the applications of Fe(acac)3 in methodology and catalysis and highlights its use for the synthesis of medicinally relevant structures and in natural product syntheses.1 Introduction2 Hydrogen Atom Transfer (HAT)3 Oxidations and Radical Transformations4 Synthesis and Use of Alkynes and Allenes5 Cross-Couplings and Cycloisomerizations6 Borylations7 Miscellaneous Reactions8 Conclusions

scholarly journals Cross-Coupling as a Key Step in the Synthesis and Structure Revision of the Natural Products Selagibenzophenones A and B

Catalysts ◽  
2021 ◽  
Vol 11 (6) ◽  
pp. 708
Author(s):  
Ringaile Lapinskaite ◽  
Štefan Malatinec ◽  
Miguel Mateus ◽  
Lukas Rycek
Keyword(s):  
Natural Products ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Biologically Active ◽  
Substitution Pattern ◽  
Partial Control ◽  
Total Syntheses ◽  
Synthetic Strategy ◽  
Methoxy Groups ◽  
Reported Data

Selagibenzophenone A (1) and its isomer selagibenzophenone B (2) were recently described as natural products from Selaginella genus plants with PDE4 inhibitory activity. Herein, we report the first total syntheses of both compounds. By comparing spectroscopic data of the synthetic compounds with reported data for the isolated material, we demonstrate that the structure of one of the two natural products was incorrectly assigned, and that in fact isolated selagibenzophenone A and selagibenzophenone B are identical compounds. The synthetic strategy for both 1 and 2 is based on a cross-coupling reaction and on the addition of organometallic species to assemble the framework of the molecules. Identifying a suitable starting material with the correct substitution pattern is crucial because its pattern is reflected in that of the targeted compounds. These syntheses are finalized via global deprotection. Protecting the phenols as methoxy groups provides the possibility for partial control over the selectivity in the demethylation thanks to differences in the reactivity of the various methoxy groups. Our findings may help in future syntheses of derivatives of the biologically active natural product and in understanding the structure–activity relationship.

From Stereodefined Cyclobutenes to Dienes: Total Syntheses of Ieodomycin D and the Southern Fragment of Macrolactin A

2015 ◽  
Vol 17 (18) ◽  
pp. 4486-4489 ◽  
Author(s):  
Caroline Souris ◽  
Antonio Misale ◽  
Yong Chen ◽  
Marco Luparia ◽  
Nuno Maulide
Keyword(s):  
Total Syntheses ◽  
Macrolactin A
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