scholarly journals Collective Total Synthesis of PPAPs: Total Synthesis of Clusianone via Intramolecular Cyclopropanation

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Masahiro Uwamori ◽  
Masahisa Nakada
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Side Chains ◽  
Total Syntheses ◽  
Cross Metathesis ◽  
Stereoselective Hydrogenation ◽  
Nonane Derivative ◽  
Stereogenic Center

The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence which has been utilized for the total syntheses of nemorosone garsubellin A and hyperforin: intramolecular cyclopropanation formation of a geminal dimethyl group and regioselective ring opening of cyclopropane. Further elaboration including chemo- and stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains was employed to complete the total synthesis of clusianone.

scholarly journals Recent Advances in Total Synthesis via Metathesis Reactions

Synthesis ◽  
2018 ◽  
Vol 50 (19) ◽  
pp. 3749-3786 ◽  
Author(s):  
Francisco Sarabia ◽  
Iván Cheng-Sánchez
Keyword(s):  
Total Synthesis ◽  
Tandem Reactions ◽  
Alkyne Metathesis ◽  
Enyne Metathesis ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Total Syntheses ◽  
Cross Metathesis ◽  
Carbon Carbon Bonds ◽  
Metathesis Reactions

The metathesis reactions, in their various versions, have become a powerful and extremely valuable tool for the formation of carbon–carbon bonds in organic synthesis. The plethora of available catalysts to perform these reactions, combined with the various transformations that can be accomplished, have positioned the metathesis processes as one of the most important reactions of this century. In this review, we highlight the most relevant synthetic contributions published between 2012 and early 2018 in the field of total synthesis, reflecting the state of the art of this chemistry and demonstrating the significant synthetic potential of these methodologies.1 Introduction2 Alkene Metathesis in Total Synthesis2.1 Total Synthesis Based on a Ring-Closing-Metathesis Reaction2.2 Total Synthesis Based on a Cross-Metathesis Reaction2.3 Strategies for Selective and Efficient Metathesis Reactions of Alkenes2.3.1 Temporary Tethered Ring-Closing Metathesis2.3.2 Relay Ring-Closing Metathesis2.3.3 Stereoselective Alkene Metathesis2.3.4 Alkene Metathesis in Tandem Reactions3 Enyne Metathesis in Total Synthesis3.1 Total Syntheses Based on a Ring-Closing Enyne-Metathesis Reaction3.2 Total Syntheses Based on an Enyne Cross-Metathesis Reaction3.3 Enyne Metathesis in Tandem Reactions4 Alkyne Metathesis in Total Synthesis4.1 Total Synthesis Based on a Ring-Closing Alkyne-Metathesis Reaction4.2 Other Types of Alkyne-Metathesis Reactions5 Conclusions

scholarly journals Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1905
Author(s):  
Satya Kumar Avula ◽  
Biswanath Das ◽  
Rene Csuk ◽  
Ahmed Al-Rawahi ◽  
Ahmed Al-Harrasi
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Present Article ◽  
Structural Features ◽  
Side Chains ◽  
Total Syntheses ◽  
Recent Advances ◽  
Long Chain

Pyranone natural products have attracted great attention in recent years from chemists and biologists due to their fascinating stereoisomeric structural features and impressive bioactivities. A large number of stereoselective total syntheses of these compounds have been described in the literature. The natural pyranones with long side chains have recently received significant importance in the synthetic field. In the present article, we aim to review the modern progress of the stereoselective total syntheses of these natural pyranones containing long-chain substituents.

Endgroup and Sidechain Functionalization of Surface-Initiated ROMP Thin Films: Progress Towards ROMP-Based Molecular Wires

2018 ◽  
Author(s):  
Nicholas Marshall
Keyword(s):  
Thin Films ◽  
Contact Angle ◽  
Cyclic Voltammetry ◽  
Polymer Films ◽  
Conjugated Polymer ◽  
Ring Opening ◽  
Molecular Wires ◽  
Metathesis Polymerization ◽  
Cross Metathesis ◽  
Active Ester

A set of experiments in surface-initiated ring-opening metathesis polymerization, including end-functionalization of growing brushes and contact angle/cyclic voltammetry measurements. We report preparation and CV of two different conjugated polymer films, and several endgroup and sidechain functionalization experiments using cross-metathesis and active ester substitution.<br>

The Total Synthesis of Rhabdastrellic Acid A

2018 ◽  
Author(s):  
Yaroslav Boyko ◽  
Christopher Huck ◽  
David Sarlah
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Side Chains ◽  
General Strategy ◽  
Modular Approach ◽  
Linear Sequence ◽  
Generating Sequence ◽  
First Time

<div>The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained <i>trans-syn-trans</i>-perhydrobenz[<i>e</i>]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a <i>p</i>-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.</div>

Concise Total Synthesis of Curvulone B

Synlett ◽  
2020 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Shivalal Banoth ◽  
Utkal Mani Choudhury ◽  
Kanakaraju Marumudi ◽  
Ajit C. Kunwar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Bond Forming ◽  
Cross Metathesis ◽  
Bond Forming Reactions ◽  
Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

scholarly journals Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3224
Author(s):  
Leander Geske ◽  
Ulrich Kauhl ◽  
Mohamed E. M. Saeed ◽  
Anja Schüffler ◽  
Eckhard Thines ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Biological Activities ◽  
Biological Evaluation ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Total Syntheses ◽  
Wittig Olefination ◽  
Starting Point ◽  
Perkin Reaction ◽  
Synthesis And Biological Evaluation

The biological activities of shancigusin C (1) and bletistrin G (2), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (1) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (2) was achieved by the Wittig olefination followed by several regioselective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (1) and bletistrin G (2) against tumor cells suggest suitability as a starting point for further structural variation.

Total syntheses and antiproliferative activities of prenostodione and its analogues

2021 ◽  
Author(s):  
Aldahir Ramos Orea ◽  
María Teresa Ramírez-Apan ◽  
Rosa M. Chávez-Santos ◽  
Rodrigo Aguayo-Ortiz ◽  
Clara I Espitia ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Indole Alkaloid ◽  
Total Syntheses ◽  
Antiproliferative Activities

A high-yielding total synthesis of the indole alkaloid prenostodione was completed in 4 steps and 44% overall yield from 1H-indole-3-carboxylic acid. The expedient syntheses of prenostodiones containing distinct substituents at...

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