scholarly journals A novel total synthesis of aculeatin A via a stepwise approach

RSC Advances ◽  
2017 ◽  
Vol 7 (16) ◽  
pp. 9813-9818 ◽  
Author(s):  
Zhibin Zhang ◽  
Xiao Leng ◽  
Shenkun Yang ◽  
Cheng Liang ◽  
Shuangping Huang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Antimalarial Activity ◽  
Synthetic Approach ◽  
Stepwise Approach

Aculeatin A, isolated from the plant Amomum aculeatum, is a dispirocyclic compound having antimalarial activity. We describe a novel synthetic approach to aculeatin A via a stepwise strategy.

General Cyclopropane Assembly via Enantioselective Redox-Active Carbene Transfer to Aliphatic Olefins

2018 ◽  
Author(s):  
Marc Montesinos-Magraner ◽  
Matteo Costantini ◽  
Rodrigo Ramirez-Contreras ◽  
Michael E. Muratore ◽  
Magnus J. Johansson ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Chemical Space ◽  
Synthetic Approach ◽  
Asymmetric Cyclopropanation ◽  
Redox Active ◽  
Wide Range ◽  
Leaving Group ◽  
Stereoelectronic Properties ◽  
Carbene Transfer

Asymmetric cyclopropane synthesis currently requires bespoke strategies, methods, substrates and reagents, even when targeting similar compounds. This limits the speed and chemical space available for discovery campaigns. Here we introduce a practical and versatile diazocompound, and we demonstrate its performance in the first unified asymmetric synthesis of functionalized cyclopropanes. We found that the redox-active leaving group in this reagent enhances the reactivity and selectivity of geminal carbene transfer. This effect enabled the asymmetric cyclopropanation of a wide range of olefins including unactivated aliphatic alkenes, enabling the 3-step total synthesis of (–)-dictyopterene A. This unified synthetic approach delivers high enantioselectivities that are independent of the stereoelectronic properties of the functional groups transferred. Our results demonstrate that orthogonally-differentiated diazocompounds are viable and advantageous equivalents of single-carbon chirons<i>.</i>

scholarly journals Microwave Heating Promotes the S-Alkylation of Aziridine Catalyzed by Molecular Sieves: A Post-Synthetic Approach to Lanthionine-Containing Peptides

Molecules ◽  
2021 ◽  
Vol 26 (20) ◽  
pp. 6135
Author(s):  
Valentina Verdoliva ◽  
Giuseppe Digilio ◽  
Michele Saviano ◽  
Stefania De Luca
Keyword(s):  
Microwave Irradiation ◽  
Molecular Sieves ◽  
Ring Opening ◽  
Cysteine Residue ◽  
Biologically Active ◽  
Synthetic Approach ◽  
Stepwise Approach ◽  
Valuable Alternative ◽  
Ring Opening Reactions ◽  
Nucleophilic Ring Opening

Aziridine derivatives involved in nucleophilic ring-opening reactions have attracted great interest, since they allow the preparation of biologically active molecules. A chemoselective and mild procedure to convert a peptide cysteine residue into lanthionine via S-alkylation on aziridine substrates is presented in this paper. The procedure relies on a post-synthetic protocol promoted by molecular sieves to prepare lanthionine-containing peptides and is assisted by microwave irradiation. In addition, it represents a valuable alternative to the stepwise approach, in which the lanthionine precursor is incorporated into peptides as a building block.

scholarly journals Total Syntheses of Pladienolide-Derived Spliceosome Modulators

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5938
Author(s):  
Jaehoon Sim ◽  
Eunbin Jang ◽  
Hyun Jin Kim ◽  
Hongjun Jeon
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Features ◽  
Synthetic Approach ◽  
Synthetic Analog ◽  
Phase I Clinical Trials ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Anti Cancer ◽  
Synthetic Approaches

Pladienolides, an emerging class of naturally occurring spliceosome modulators, exhibit interesting structural features, such as highly substituted 12-membered macrocycles and epoxide-containing diene side chains. The potential of pladienolides as anti-cancer agents is confirmed by H3B-8800, a synthetic analog of this natural product class, which is currently under Phase I clinical trials. Since its isolation in 2004 and the first total synthesis in 2007, a dozen total syntheses and synthetic approaches toward the pladienolide class have been reported to date. This review focuses on the eight completed total syntheses of naturally occurring pladienolides or their synthetic analogs, in addition to a synthetic approach to the main framework of the natural product.

Total synthesis and antimalarial activity of mortiamides A–D

2019 ◽  
Vol 55 (52) ◽  
pp. 7434-7437 ◽  
Author(s):  
Christopher Bérubé ◽  
Dominic Gagnon ◽  
Alexandre Borgia ◽  
Dave Richard ◽  
Normand Voyer
Keyword(s):  
Plasmodium Falciparum ◽  
Total Synthesis ◽  
Resistant Strain ◽  
Antimalarial Activity ◽  
Drug Resistant

This work describes the first total synthesis of mortiamides and their anti-malarial activity against a multi-drug resistant strain of Plasmodium falciparum.

scholarly journals Revision of the Structure and Total Synthesis of Topsentin C

Synthesis ◽  
2017 ◽  
Vol 49 (11) ◽  
pp. 2562-2574 ◽  
Author(s):  
Nikita Golantsov ◽  
Alexey Festa ◽  
Alexey Varlamov ◽  
Leonid Voskressensky
Keyword(s):  
Total Synthesis ◽  
Secondary Metabolite ◽  
Conjugate Addition ◽  
Solvent Free ◽  
Synthetic Approach ◽  
Protecting Group ◽  
Marine Alkaloids ◽  
Mild Reduction

An efficient synthetic approach to access (indol-3-yl)ethane-1,2-diamines with a protecting group at the indole N atom from readily available 3-(2-nitrovinyl)indoles is reported. This approach includes solvent-free conjugate addition of O-pivaloylhydroxylamines to 1-Boc-3-(2-nitrovinyl)indoles followed by mild reduction of the adducts. The obtained (indol-3-yl)ethane-1,2-diamines are convenient synthetic precursors for several classes of marine alkaloids. The first total synthesis of racemic topsentin C, a secondary metabolite from Hexadella sp., based on this approach is reported. The initially proposed structure for topsentin C has been revised.

Synthetic Approach Toward the Total Synthesis of Kempane Diterpenes via Transannular Diels−Alder Strategy

2006 ◽  
Vol 71 (19) ◽  
pp. 7370-7377 ◽  
Author(s):  
Franck Caussanel ◽  
Keyan Wang ◽  
Sreekanth A. Ramachandran ◽  
Pierre Deslongchamps
Keyword(s):  
Total Synthesis ◽  
Diels Alder ◽  
Synthetic Approach

Bioinspired total synthesis of (−)-gymnothelignan L

2018 ◽  
Vol 5 (7) ◽  
pp. 1124-1128 ◽  
Author(s):  
Peng Chen ◽  
Liang Huo ◽  
Huilin Li ◽  
Lin Liu ◽  
Ziyun Yuan ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Synthetic Approach ◽  
Asymmetric Total Synthesis

The first asymmetric total synthesis of gymnothelignan L has been accomplished in 14 steps with 11.2% overall yield. The synthetic approach features an anti Evans aldol reaction, a diastereoselective methylation, a Suzuki–Miyaura coupling and a bioinspired desymmetric transannular Friedel–Crafts reaction.

Studies Directed Towards the Total Synthesis of Anticapsin. X-Ray Crystal-Structure of (1RS,2SR,4RS,5RS,6SR)-5-Hydroxy-2-phthalimido-1-trimethylsilyloxy-bicyclo[2.2.2]octane-2,6-carbolactone

1990 ◽  
Vol 43 (11) ◽  
pp. 1827 ◽  
Author(s):  
MJ Crossley ◽  
TW Hambley ◽  
AW Stamford
Keyword(s):  
Crystal Structure ◽  
Amino Acid ◽  
Total Synthesis ◽  
Synthetic Approach ◽  
Hydrogen Atoms ◽  
Full Matrix ◽  
X Ray ◽  
X Ray Crystallography ◽  
Relative Stereochemistry ◽  
Atomic Parameters

The relative stereochemistry of methyl 2-phthalimido-1- trimethylsilyloxybicyclo[2.2.2]oct-5-ene-2-carboxylate (9) and its 5,6-epoxide (10), intermediates in a synthetic approach to the amino acid antibiotic anticapsin, were established by the TiCl4-mediated cyclization of (10) to the carbolactone (12); the structure of which was proved by single-crystal X-ray crystallography. Full-matrix least- squares refinement of all atomic parameters with individual isotropic thermal parameters for the hydrogen atoms by using 1446 reflections converged at R 0.036. Crystals of (12) are monoclinic, P21/c, a 12.342(3), b 12.239(2), c 13.405(3) Ǻ, β 99.34(2)°, Z 4.

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