First Total Synthesis of Isopsoralenoside

2022 ◽  
Vol 19 ◽  
Author(s):  
Min Wu ◽  
Lijia Xu ◽  
Mingwei, Song ◽  
Ying, Li ◽  
Yingying Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Ultraviolet Light ◽  
Butyl Alcohol ◽  
Alcohol Extract ◽  
Key Steps

Abstract: The first total synthesis of the natural product iopsoralenoside, isolated from the n-butyl alcohol extract of Fructus Psoraleae (FP), was achieved in 17% yield over 7 steps. The key steps of the process are the glycosylation and irradiation promoted by ultraviolet light. This synthesis provides a sufficient amount of synthesized trans- and cis-isopsoralenoside for further bioassays.

scholarly journals Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one from L-Malic Acid

2018 ◽  
Vol 13 (7) ◽  
pp. 1934578X1801300
Author(s):  
Dandekar Chandrakanth ◽  
Yerragorla Gopala Rao ◽  
Tallapally Swamy ◽  
Dhanraj O Biradar ◽  
Lonavath Vishnupriya ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Malic Acid ◽  
Ring Closing Metathesis ◽  
Stereoselective Reduction ◽  
Key Steps ◽  
Barbier Allylation

A stereoselective total synthesis of an antiproliferative and antifungal natural product, (6 S)-5,6-dihydro-6-[(2 R)-2-hydroxy-6-phenylhexyl]-2 H-pyran-2-one has been accomplished using the Barbier allylation, LiAlH4/LiI mediated syn-stereoselective reduction and olefin ring-closing metathesis (RCM) as the key steps. L-Malic acid was used as a chiral precursor for the construction of syn-1,3-diol moiety of the molecule.

The Structure Elucidation of Haprolid

Synthesis ◽  
2017 ◽  
Vol 50 (03) ◽  
pp. 529-538 ◽  
Author(s):  
Markus Kalesse ◽  
Jun Li ◽  
Jun Xing ◽  
Daniel Lücke ◽  
Dennis Lübken ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structure Elucidation ◽  
Carcinoma Cell ◽  
Hidden Markov ◽  
Biological Evaluation ◽  
Terminal Olefin ◽  
Carcinoma Cell Lines ◽  
Hepatocellular Carcinoma Cell ◽  
Key Steps

The assignment of two stereocenters of the natural product haprolid through the application of a profile hidden Markov model (HMM) and its confirmation through total synthesis of the natural product and of two of its diastereomers are reported. The structure elucidation of this polyketide-peptide hybrid natural product is a telling showcase of how difficult it can be to determine the absolute configuration of isolated stereocenters and the benefits of a gene cluster analysis for structure determination. The key steps of the synthesis are a selective epoxidation of a terminal olefin and the stereodivergent macrolactonization strategy. Furthermore, the biological evaluation of all products showed that all diastereomers are potent inhibitors of hepatocellular carcinoma cell lines.

Enantioselective total synthesis of (S)-nakinadine B

RSC Advances ◽  
2016 ◽  
Vol 6 (31) ◽  
pp. 25913-25917 ◽  
Author(s):  
Yuvraj Garg ◽  
Satyendra Kumar Pandey
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Michael Addition ◽  
Marine Natural Product ◽  
Enantioselective Total Synthesis ◽  
Novel Approach ◽  
Key Steps

A novel approach for the synthesis of (S)-nakinadine B, a marine natural product is described. The synthesis utilizes the optimized combination of organocatalyzed Michael addition and aminoxylation reactions as key steps.

Total Synthesis of (–)-Aristoquinoline via an Intramolecular Nitrilium Ion Cyclization

Synthesis ◽  
2021 ◽  
Author(s):  
Keith P. Reber ◽  
Priyansh D. Gujarati
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Building Block ◽  
Spectroscopic Properties ◽  
Ring System ◽  
Synthetic Route ◽  
Enantioselective Total Synthesis ◽  
Key Steps

AbstractThe enantioselective total synthesis of the alkaloid aristoquinoline has been achieved in seven steps and 26% overall yield. A new preparation of the useful synthetic building block (–)-α-terpinyl amine was also developed in order to avoid stoichiometric mercury reagents or azide-containing intermediates. Key steps in the optimized synthetic route include an intramolecular nitrilium ion cyclization to form the characteristic azabicyclo[3.3.1]nonane ring system and a dia­stereoselective reduction of the resulting imine mixture to afford the natural product. An isomer of aristoquinoline containing an exocyclic alkene was also obtained and found to exhibit unusual chromatographic and spectroscopic properties.

A tosyliminium ion-based total synthesis of (±)-schefferine

2000 ◽  
Vol 78 (9) ◽  
pp. 1165-1169 ◽  
Author(s):  
Darío A Bianchi ◽  
Teodoro S Kaufman
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Dimethyl Ether ◽  
Key Steps

The synthesis of the phenolic tetrahydroprotoberberine alkaloid (±)-schefferine is reported, featuring as key steps a tosyliminium ion-mediated Friedel-Crafts alkylation of eugenol dimethyl ether and an intramolecular Mitsunobu-type amination.Key words: total synthesis, (±)-schefferine, natural product, tosyliminium ion, Mitsunobu amination.

A Chemoenzymatic Total Synthesis of the Undecenolide ( - )-Cladospolide C

2005 ◽  
Vol 58 (7) ◽  
pp. 511 ◽  
Author(s):  
Martin G. Banwell ◽  
David T. J. Loong ◽  
Anthony C. Willis
Keyword(s):  
Total Synthesis ◽  
Single Crystal ◽  
Natural Product ◽  
Absolute Configuration ◽  
Starting Material ◽  
Unsaturated Ester ◽  
Ring Closing Metathesis ◽  
X Ray ◽  
Key Steps ◽  
First Time

The (−)-enantiomer, ent-3, of the natural product (+)-cladospolide C (3) has been prepared for the first time using the monochiral cis-1,2-dihydrocatechol 5 as starting material. Key steps include coupling of the derived acid 6 with the enzymatically generated (S)-(+)-4-penten-2-ol (7) and ring-closing metathesis (RCM) of the resultant doubly unsaturated ester 8 to give lactone 9. The structure of this last compound has been confirmed by single-crystal X-ray analysis. This work has established that the absolute configuration of (+)-cladospolide C has been correctly assigned and is as illustrated in structure 3.

Applications of crotyldiisopinocampheylboranes in synthesis: a formal total synthesis of (+)-calyculin A

2001 ◽  
Vol 79 (11) ◽  
pp. 1562-1592 ◽  
Author(s):  
Oren P Anderson ◽  
Anthony GM Barrett ◽  
Jeremy J Edmunds ◽  
Shun-Ichiro Hachiya ◽  
James A Hendrix ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Marine Natural Product ◽  
Aldol Reactions ◽  
Calyculin A ◽  
Coupling Reactions ◽  
Stille Coupling ◽  
Palladium Catalyzed ◽  
Key Steps ◽  
Absolute Stereochemistry

The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth–Meyers approach to the synthesis of the oxazole fragment.Key words: calyculin, marine natural product, phosphatase inhibitor, total synthesis, palladium catalyzed coupling reactions, allylboration reactions, aldol reactions, spiroketal, Cornforth–Meyers oxazole reaction.

scholarly journals Total Synthesis of Oxepin and Dihydrooxepin Containing Natural Products

Synthesis ◽  
2021 ◽  
Author(s):  
Thomas Magauer ◽  
Kevin Rafael Sokol
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Radical Cyclization ◽  
Sigmatropic Rearrangement ◽  
Natural Product Synthesis ◽  
Synthetic Methods ◽  
Acid Catalyzed ◽  
Metal Catalyzed ◽  
Key Steps

AbstractThe construction of oxepin and dihydrooxepin containing natural products represents a challenging task in total synthesis. In the last decades, a variety of synthetic methods have been reported for the installation of these structural motifs. Herein, we provide an overview of synthetic methods and strategies to construct these motifs in the context of natural product synthesis and highlight the key steps of each example.1 Introduction2 Oxepin Natural Products3 Dihydrooxepin Natural Products3 Brønsted or Lewis acid Catalyzed Cyclization3.2 Radical Cyclization3.3 Substitution and Addition Cyclization3.4 Sigmatropic Rearrangement3.5 Oxidative Methods3.6 Transition Metal Catalyzed Cyclization4 Summary

Sonogashira coupling in natural product synthesis

2014 ◽  
Vol 1 (5) ◽  
pp. 556-566 ◽  
Author(s):  
Dan Wang ◽  
Shuanhu Gao
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Sonogashira Coupling ◽  
Key Steps

This review will focus on selected applications of Sonogashira coupling and subsequent transformations as key steps in the total synthesis of natural products.

First Total Synthesis of 27-deoxylyngbyabellin A

Synthesis ◽  
2021 ◽  
Author(s):  
Yang Zhang ◽  
Yi Liu ◽  
Yuguo Du
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Secondary Metabolite ◽  
Building Block ◽  
Aldol Reaction ◽  
Cascade Reaction ◽  
Hydroxy Ester ◽  
Marine Cyanobacteria ◽  
One Pot ◽  
Key Steps

In this study, we documented the first total synthesis of marine cyanobacteria secondary metabolite 27-deoxylyngbyabellin A in 10 linear steps with 9.7% overall yield. Key steps entailed (1) one-pot cascade reaction of (S)-2-(benzyloxy)-3-methylbutanoic acid and Boc-Ile-Thz-OMe with the building block β-azido disulfide 7 to access the critical thiazole units 3 and 4, (2) chiral oxazaborolidinone-mediated asymmetry aldol reaction to construct (S)-β-hydroxy ester 5, and (3) DPPA-mediated macrolactamization of linear precursor 2 to achieve the natural product 27-deoxylyngbyabellin A.

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