Total Synthesis of Spongistatin 1: A Synthetic Strategy Exploiting Its Latent Pseudo-Symmetry

2005 ◽  
Vol 117 (34) ◽  
pp. 5569-5574 ◽  
Author(s):  
Matthew Ball ◽  
Matthew J. Gaunt ◽  
David F. Hook ◽  
Alan S. Jessiman ◽  
Shigeru Kawahara ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Spongistatin 1 ◽  
Synthetic Strategy

Total Synthesis of Spongistatin 1: A Synthetic Strategy Exploiting Its Latent Pseudo-Symmetry

2005 ◽  
Vol 44 (34) ◽  
pp. 5433-5438 ◽  
Author(s):  
Matthew Ball ◽  
Matthew J. Gaunt ◽  
David F. Hook ◽  
Alan S. Jessiman ◽  
Shigeru Kawahara ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Spongistatin 1 ◽  
Synthetic Strategy

Computationally Augmented Retrosynthesis: Total Synthesis of Paspaline A and Emindole PB

2018 ◽  
Author(s):  
Timothy Newhouse ◽  
Daria E. Kim ◽  
Joshua E. Zweig
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Small Molecules ◽  
First Principles ◽  
Quantum Chemical ◽  
Computational Analysis ◽  
Empirical Evaluation ◽  
Synthetic Strategy ◽  
Catalyzed Reactions ◽  
Enzyme Catalyzed Reactions

The diverse molecular architectures of terpene natural products are assembled by exquisite enzyme-catalyzed reactions. Successful recapitulation of these transformations using chemical synthesis is hard to predict from first principles and therefore challenging to execute. A means of evaluating the feasibility of such chemical reactions would greatly enable the development of concise syntheses of complex small molecules. Herein, we report the computational analysis of the energetic favorability of a key bio-inspired transformation, which we use to inform our synthetic strategy. This approach was applied to synthesize two constituents of the historically challenging indole diterpenoid class, resulting in a concise route to (–)-paspaline A in 9 steps from commercially available materials and the first pathway to and structural confirmation of emindole PB in 13 steps. This work highlights how traditional retrosynthetic design can be augmented with quantum chemical calculations to reveal energetically feasible synthetic disconnections, minimizing time-consuming and expensive empirical evaluation.

The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: fragment couplings, completion of the synthesis, analogue generation and biological evaluation

2005 ◽  
Vol 3 (13) ◽  
pp. 2431 ◽  
Author(s):  
Ian Paterson ◽  
David Y.-K. Chen ◽  
Mark J. Coster ◽  
José L. Aceña ◽  
Jordi Bach ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Biological Evaluation ◽  
Spongistatin 1 ◽  
Altohyrtin A

scholarly journals Towards the total synthesis of keramaphidin B

2016 ◽  
Vol 12 ◽  
pp. 1096-1100 ◽  
Author(s):  
Pavol Jakubec ◽  
Alistair J M Farley ◽  
Darren J Dixon
Keyword(s):  
Total Synthesis ◽  
Michael Addition ◽  
Synthetic Strategy

The enantio- and diastereoselective Michael addition of a δ-valerolactone-derived pronucleophile to a substituted furanyl nitroolefin catalysed by a bifunctional cinchonine-derived thiourea has been used as the key stereocontrolling step in a new synthetic strategy to the heavily functionalised piperidine core of keramaphidin B.

scholarly journals The efficient synthesis of 1-deoxymannojirimycin and its derivatives

2021 ◽  
Author(s):  
◽  
Benjamin Mark Mandinka Deeble
Keyword(s):  
Total Synthesis ◽  
Lysosomal Storage Diseases ◽  
Heterocyclic Ring ◽  
Lysosomal Storage ◽  
Synthetic Strategy ◽  
Anti Cancer ◽  
Structural Analogues ◽  
Treatment Of Diabetes ◽  
Significant Effort ◽  
Selection Of

<p>Azasugars are structural analogues of carbohydrates whereby the oxygen in the heterocyclic ring is substituted for a nitrogen. These carbohydrates are an important class of compounds with medicinal bioactivities and have shown potential for the treatment of diabetes, viral-infection, cancers, and lysosomal storage diseases. 1-deoxymannojirimycin (DMJ), is a mannosidase inhibiting azasugar which has shown anti-cancer and anti-viral activity. There has been significant effort put towards developing methodology to produce this compound and libraries of its derivatives. This thesis presents the synthesis of DMJ and a selection of its derivatives via an efficient 4 step methodology from a carbohydrate starting material, exploiting chemo and regioselective reactions to allow for a total synthesis with minimal use of protecting groups. The synthesis of DMJ, using the methodology developed herein, surpasses published syntheses in efficiency. This synthetic strategy was then used for the preparation of N-functionalised DMJ derivatives without the requirement of additional synthetic steps. To illustrate the versatility of this methodology, a selection of derivatives incorporating different functionalities have been synthesised.</p>

Total Synthesis of (–)-Strempeliopine via Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

2021 ◽  
Author(s):  
Yi An ◽  
Mengjuan Wu ◽  
Weijian Li ◽  
Yaling Li ◽  
Zhenzhen Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Enantioselective Total Synthesis ◽  
Synthetic Strategy ◽  
Palladium Catalyzed ◽  
The Absolute ◽  
Set Up

Reported herein a concise and enantioselective total synthesis of Schizozygine alkaloids (–)-strempeliopine. This synthetic strategy features a palladium-catalyzed decarboxylative asymmetric allylic alkylation of N-benzoyl lactam to set up the absolute...

Total Synthesis of DHA and DPAn-3 non-enzymatic oxylipins

Synthesis ◽  
2021 ◽  
Author(s):  
alexandre guy ◽  
Jérémy Merad ◽  
Thomas Degrange ◽  
Guillaume Reversat ◽  
Valérie Bultel-Poncé ◽  
...  
Keyword(s):  
Oxidative Stress ◽  
Fatty Acids ◽  
Docosahexaenoic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Total Synthesis ◽  
Biological Properties ◽  
Chemical Structures ◽  
Structural Variety ◽  
Synthetic Strategy

Oxylipins are formed in-vivo from polyunsaturated fatty acids (PUFAs). A large structural variety of compounds is grouped under the term oxylipins, which differ from their formation mechanism (involving enzymes or not), as well as their chemical structures (cyclopentanes, tetrahydrofurans, hydroxylated-PUFA etc.). All structures of oxylipins are of great biological interests. Directly correlated to oxidative stress phenomenon, non-enzymatic oxylipins are used as systemic and/or specific biomarkers in various pathologies and more especially, they were found to have their own biological properties. Produced in-vivo as a non-separable mixture of isomers, total synthesis is a keystone to answer biological questions. In this work, we described the total synthesis of three non-enzymatic oxylipins derived from docosahexaenoic acid (DHA) and docosapentanoic acid (DPAn-3) using a unique and convergent synthetic strategy.

scholarly journals First Total Synthesis and Investigation of the X-ray Crystal Structure of the Pyrano[3,2-a]carbazole Alkaloid Clausenalansine A

Synthesis ◽  
2020 ◽  
Vol 53 (02) ◽  
pp. 359-364
Author(s):  
Hans-Joachim Knölker ◽  
Valerie Lösle ◽  
Olga Kataeva
Keyword(s):  
Crystal Structure ◽  
Total Synthesis ◽  
Lewis Acid ◽  
Oxidative Cyclization ◽  
Formyl Group ◽  
Pyran Ring ◽  
X Ray ◽  
Synthetic Strategy

AbstractWe describe the first total synthesis of the recently discovered pyrano[3,2-a]carbazole alkaloid clausenalansine A. The synthetic strategy for the construction of this formylpyrano[3,2-a]carbazole is based on a sequence of Buchwald–Hartwig coupling, palladium(II)-catalyzed oxidative cyclization, Lewis acid promoted annulation of the pyran ring, and chemoselective oxidation of a methyl to a formyl group.

Total Synthesis of (–)-Alstofolinine A: Selected Furan Oxidation/ Cyclization Cascade

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 7-12 ◽  
Author(s):  
Ye Zhang ◽  
Lei Zhang ◽  
Xiangbing Qi
Keyword(s):  
Total Synthesis ◽  
Common Core ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Asymmetric Total Synthesis ◽  
Ring Systems ◽  
Synthetic Strategy ◽  
Nucleophilic Addition Reaction

Indole-fused tetracyclic ring systems containing nitrogen atoms are common core skeletons of many indole alkaloids such as sarpagine, macroline, and ajmaline. Efficient and stereoselective construction of these ring systems can promote the development of the corresponding alkaloid syntheses. In this article, we briefly summarize our current progress toward the application of the aza-Achmatowicz reaction and indole nucleophilic addition reaction cascade for the first asymmetric total synthesis of the macroline-type indole alkaloid (–)-Alstofolinine A. Our synthetic strategy is based on furan oxidation/rearrangement and proceeds from easily accessible materials such as indole and furan derivatives.

Sign in / Sign up

Export Citation Format

Share Document