General Asymmetric Synthetic Strategy for the α-Alkylated 2,5,6-Trisubstituted Pyran of Indanomycin and Related Natural Products

2020 ◽  
Vol 2020 (13) ◽  
pp. 1947-1955
Author(s):  
Ravishetty Padma ◽  
Beduru Srinivas ◽  
Jhillu S. Yadav ◽  
Debendra K. Mohapatra
Keyword(s):  
Natural Products ◽  
Synthetic Strategy

scholarly journals Development of a Divergent Route to Erythrina Alkaloids

Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 327-333 ◽  
Author(s):  
Jesper L. Kristensen ◽  
Sebastian Clementson ◽  
Mikkel Jessing ◽  
Paulo J. Vital
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
19Th Century ◽  
First Generation ◽  
Second Generation ◽  
Enantioselective Synthesis ◽  
Third Generation ◽  
Synthetic Strategy ◽  
Erythrina Alkaloids ◽  
The 19Th Century

Erythrina alkaloids were identified at the end of the 19th century and today, more than 100 members of the erythrinane family have been isolated. They are characterized by a unique tetracyclic, α-tertiary spiroamine scaffold. Herein we detail our efforts towards the development of a divergent enantioselective synthesis of (+)-dihydro-β-erythroidine (DHβE) – one of the most prominent members of this intriguing family of natural products.1 Introduction2 Synthetic Strategy2.1 First Generation2.2 Second Generation2.3 Third Generation2.3.1 Radical Endgame2.3.2 Completion of the Total Synthesis3 Conclusion

scholarly journals Concise and Gram-Scale Total Synthesis of Lansiumamides A and B and Alatamide

Molecules ◽  
2019 ◽  
Vol 24 (20) ◽  
pp. 3764
Author(s):  
Ran Lin ◽  
Xi Lin ◽  
Qian Su ◽  
Binbin Guo ◽  
Yanqin Huang ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Synthetic Strategy

The total synthesis of potent anti-obesity lansiumamide B was accomplished in four steps using commercially available materials. The synthetic strategy, featured with copper-catalyzed Buchwald coupling, is concise, convergent, practical and can be carried out on a one-gram scale. This approach could give either Z- or E-configured enamide moiety in natural products with absolute stereocontrol and was applied in the total synthesis of natural products.

scholarly journals Synthesis of Highly Functionalised Furo[3,4-b]pyrans: Towards the Fungal Metabolite (−)-TAN-2483B

2021 ◽  
Author(s):  
◽  
R.M. Kalpani K. Somarathne
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Cyclopropane Ring ◽  
Ring Expansion ◽  
Ethyl Esters ◽  
Pyran Ring ◽  
Synthetic Strategy ◽  
Alternative Approach ◽  
Synthetic Approaches

<p>Carbohydrate-derived cyclopropanes combine both the stereochemical wealth of carbohydrates and the reactivity of cyclopropanes. A diverse variety of reaction modes for these cyclopropyl carbohydrates can be harnessed for the synthesis of natural products and other targets.  The natural products (−)-TAN-2483A and (−)-TAN-2483B are fungal secondary metabolites displaying a variety of bioactivities such as inhibition of c-src kinase action and parathyroid hormone-induced bone resorption. This thesis described several synthetic approaches to the natural product (−)-TAN-2483B and analogues of (−)-TAN-2483B employing cyclopropane ring expansion.  The synthetic route to (−)-TAN-2483B began with the readily available substrate D-mannose. The pyran ring unsaturation of the natural product was established by a cyclopropanation-ring expansion sequence. A synthetic strategy via dichlorocyclopropane-based intermediates is described in chapter 2. This being unsuccessful, an alternative approach via 2-fomyl-glycal was developed in chapter 3. The chapter 2 and 3 provided a solid background for the achievement of the analogues synthesis illustrated in chapter 4 via dibromocyclopropane. Lewis acid-mediated alkynylation followed by Pdcatalysed carbonylative lactonisation was successfully utilised in the revelation of the furo[3,4-b]pyran ring skeleton. This route afforded analogues of TAN-2483B; the Z-and E-unsaturated ethyl esters 140 and 141 and hydroxy(−)-TAN-2483B 145. The total synthesis of (−)-TAN-2483B was not achieved due to unforeseen obstacles encountered in the deoxygenation of the side arm of 335 (Chapter 4) into the E-propenyl side arm of (−)-TAN-2483B.</p>

An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides

2017 ◽  
Vol 2017 (13) ◽  
pp. 1704-1712 ◽  
Author(s):  
Taejung Kim ◽  
Kyu Hyuk Jeong ◽  
Ki Sung Kang ◽  
Masaya Nakata ◽  
Jungyeob Ham
Keyword(s):  
Natural Products ◽  
Synthetic Strategy

The intramolecular Diels–Alder reaction: recent advances and synthetic applications

1984 ◽  
Vol 62 (2) ◽  
pp. 183-234 ◽  
Author(s):  
Alex G. Fallis
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Synthetic Strategy ◽  
Diels Alder Reaction ◽  
Recent Advances ◽  
Cyclic Dienes

Recent advances and examples of the intramolecular Diels–Alder reaction are summarized and applications to the total synthesis of natural products, both completed and in progress, noted. A detailed discussion of trienes leading to bicyclo[4.3.0]nonene skeletons is followed by examples of bicyclo[4.4.0]decenes and adducts arising from ortho-quinodimethane precursors. Cycloadditions affording bicyclo[n.4.0] systems and bridged-ring adducts from cyclic dienes conclude this survey which is followed by a discussion of unreactive trienes and a brief analysis of synthetic strategy to complete the review.

scholarly journals Total Synthesis of the Natural Chalcone Lophirone E, Synthetic Studies toward Benzofuran and Indole-Based Analogues, and Investigation of Anti-Leishmanial Activity

Molecules ◽  
2022 ◽  
Vol 27 (2) ◽  
pp. 463
Author(s):  
Luca Pozzetti ◽  
Roberta Ibba ◽  
Sara Rossi ◽  
Orazio Taglialatela-Scafati ◽  
Donatella Taramelli ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Leishmania Infantum ◽  
Anticancer Properties ◽  
Synthetic Strategy ◽  
Pathological Conditions ◽  
Structure Activity ◽  
Small Set ◽  
Synthetic Approaches ◽  
Therapeutic Leads

The potential of natural and synthetic chalcones as therapeutic leads against different pathological conditions has been investigated for several years, and this class of compounds emerged as a privileged chemotype due to its interesting anti-inflammatory, antimicrobial, antiviral, and anticancer properties. The objective of our study was to contribute to the investigation of this class of natural products as anti-leishmanial agents. We aimed at investigating the structure–activity relationships of the natural chalcone lophirone E, characterized by the presence of benzofuran B-ring, and analogues on anti-leishmania activity. Here we describe an effective synthetic strategy for the preparation of the natural chalcone lophirone E and its application to the synthesis of a small set of chalcones bearing different substitution patterns at both the A and heterocyclic B rings. The resulting compounds were investigated for their activity against Leishmania infantum promastigotes disclosing derivatives 1 and 28a,b as those endowed with the most interesting activities (IC50 = 15.3, 27.2, 15.9 μM, respectively). The synthetic approaches here described and the early SAR investigations highlighted the potential of this class of compounds as antiparasitic hits, making this study worthy of further investigation.

scholarly journals Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and Derivatives

Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1406 ◽  
Author(s):  
Eva Schütznerová ◽  
Anna Krchňáková ◽  
Viktor Krchňák
Keyword(s):  
Natural Products ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Tetramic Acid ◽  
Enol Ethers ◽  
Phase Synthesis ◽  
Wang Resin ◽  
Synthetic Strategy ◽  
Solid Phase Organic Synthesis ◽  
Acid Labile

In solid-phase organic synthesis, Wang resin is traditionally used for the immobilization of acids, alcohols, phenols, and amines. We report the use of Wang resin for the traceless synthesis of ketones via acid-labile enol ethers. We demonstrate the practicality of this synthetic strategy on the solid-phase synthesis of pyrrolidine-2,4-diones, which represent the core structure of several natural products, including tetramic acid. Base-triggered condensation of pyrrolidine-2,4-diones yielded 4-hydroxy-1,1′,2′,5-tetrahydro-2H,5′H-[3,3′-bipyrrole]-2,5′-diones.

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