First total synthesis of the highly potent antitumor lactones 8-chlorogoniodiol and parvistone A: Exploiting a bioinspired late-stage epoxide ring-opening

2017 ◽  
Vol 28 (2) ◽  
pp. 246-249 ◽  
Author(s):  
Perla Ramesh ◽  
Yarram Narasimha Reddy ◽  
Thatikonda Narendar Reddy ◽  
Navuluri Srinivasu
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Ring Opening ◽  
Epoxide Ring ◽  
Epoxide Ring Opening

Asymmetric total synthesis of cryptoconcatone I

2019 ◽  
Vol 17 (14) ◽  
pp. 3552-3566 ◽  
Author(s):  
Ranjan Kumar Acharyya ◽  
Pratik Pal ◽  
Shrestha Chatterjee ◽  
Samik Nanda
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Ring Opening ◽  
Epoxide Ring ◽  
Asymmetric Total Synthesis ◽  
Epoxide Ring Opening ◽  
Cascade Cyclization ◽  
Naturally Occurring

An efficient asymmetric total synthesis of naturally occurring γ-Z-butenolide cryptoconcatone I was achieved by employing substrate-directed reductive epoxide ring opening and late-stage “Pd–Cu” catalyzed cascade cyclization.

Total synthesis of the proposed structure of a polyketide from Phialomyces macrosporus

2015 ◽  
Vol 51 (17) ◽  
pp. 3586-3589 ◽  
Author(s):  
Hideki Abe ◽  
Satoko Itaya ◽  
Kei Sasaki ◽  
Toyoharu Kobayashi ◽  
Hisanaka Ito
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Furan Ring ◽  
Epoxide Ring ◽  
Epoxide Ring Opening

Total synthesis of the proposed structure of a polyketide isolated from Phialomyces macrosporus was accomplished. This synthesis features chemoselective epoxidation, regioselective epoxide ring opening, chemo- and diastereoselective dihydroxylation, and vinylation of lactone accompanied by the formation of a furan ring.

Studies on the Total Synthesis of Antibiotic Macrolactin S: A Conventional Approach for the Synthesis of the C1–C9 and C10–C24 Fragments

Synthesis ◽  
2017 ◽  
Vol 50 (03) ◽  
pp. 663-675
Author(s):  
Pabbaraja Srihari ◽  
Ramakrishna Sayini
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Addition Reaction ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Ring Opening Reaction ◽  
Nucleophilic Addition Reaction ◽  
Convergent Approach ◽  
Key Steps

The C1–C9 and C10–C24 segments of the 24-membered polyene macrolide macrolactin S were synthesized by routes involving an epoxide-ring-opening reaction, an Ohira–Bestmann alkyne formation, a chelation-controlled nucleophilic addition reaction, and a Still–Gennari olefination as key steps. A chiron approach , starting from readily available glucose diacetonide, was used to synthesize a key intermediate, and a convergent approach was adopted for the synthesis of the key C10–C24 fragment.

A protecting group free and scalable approach towards total synthesis of (−)-venlafaxine

RSC Advances ◽  
2014 ◽  
Vol 4 (28) ◽  
pp. 14468-14470 ◽  
Author(s):  
Subhash P. Chavan ◽  
Kailash P. Pawar ◽  
Sumanta Garai
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Epoxide Ring ◽  
Protecting Group ◽  
Asymmetric Total Synthesis ◽  
Epoxide Ring Opening ◽  
Key Steps

A protecting group free asymmetric total synthesis of (−)-venlafaxine is reported. The strategy employs Sharpless epoxidation and regio-selective epoxide ring opening by an in situ generated Gilman reagent as key steps. This paper reports a 53% overall yield in 6 steps for total synthesis of (−)-venlafaxine.

scholarly journals Studies on asymmetric total synthesis of (−)-β-hydrastine via a chiral epoxide ring-opening cascade cyclization strategy

RSC Advances ◽  
2020 ◽  
Vol 10 (32) ◽  
pp. 18953-18958
Author(s):  
Jihui Li ◽  
Tianxiao Wu ◽  
Xinjing Song ◽  
Yang Zheng ◽  
Jiaxin Meng ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Enantioselective Synthesis ◽  
Epoxide Ring ◽  
Asymmetric Total Synthesis ◽  
Epoxide Ring Opening ◽  
Cascade Cyclization ◽  
The Core

Herein, both CF3COOH-catalyzed (86% ee) and KHMDS-catalyzed (78% ee) chiral epoxide ring-opening cascade cyclization to facile and enantioselective synthesis of the core phthalide tetrahydroisoquinoline scaffold of (−)-β-hydrastine are described.

Bimetallic Radical Redox-Relay Catalysis for the Isomerization of Epoxides to Allylic Alcohols

2019 ◽  
Author(s):  
Ke-Yin Ye ◽  
Terry McCallum ◽  
Song Lin
Keyword(s):  
Ring Opening ◽  
High Reactivity ◽  
Hydrogen Atom Transfer ◽  
Organic Radicals ◽  
Epoxide Ring ◽  
Allylic Alcohols ◽  
Epoxide Ring Opening ◽  
Bond Forming ◽  
Co Catalysts ◽  
The Rich

Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely bimetallic radical redox-relay, in the regio- and stereoselective rearrangement of epoxides to allylic alcohols. This approach exploits the rich redox chemistry of Ti and Co complexes and merges reductive epoxide ring opening (initiation) with hydrogen atom transfer (termination). Critically, upon effecting key bond-forming and -breaking events, Ti and Co catalysts undergo proton-transfer/electron-transfer with one another to achieve turnover, thus constituting a truly synergistic dual catalytic system.<br>

Construction the A-B bicyclic ring structure of Stemocurtisisne

2020 ◽  
Vol 17 ◽  
Author(s):  
Duc Dau Xuan
Keyword(s):  
Glutamic Acid ◽  
Natural Product ◽  
Mannich Reaction ◽  
Boronic Acid ◽  
Ring Opening ◽  
Ring Structure ◽  
Starting Material ◽  
Epoxide Ring ◽  
Epoxide Ring Opening

: The synthesis of the A-B bicyclic ring structure 3 of the natural product Stemocurtisine is described. The synthesis was accomplished in seven synthetic steps from commercially available L-glutamic acid. The key step involved a borono-Mannich reaction between the hemiaminal 6 and trans-β-styryl boronic acid and trans-β-styrylpotassiumtrifluoroborate to prepare the cis diene 4. Attempts to prepare the A-B-C ring compound 2 via intramolecular epoxide ring opening followed by rearangement under different basic conditions were unsuccessful. Only unreactive starting material was recovered.

scholarly journals Thermal and Electrochemical Properties of Solid Polymer Electrolytes Prepared via Lithium Salt-Catalyzed Epoxide Ring Opening Polymerization

2021 ◽  
Vol 11 (4) ◽  
pp. 1561
Author(s):  
Gabrielle Foran ◽  
Nina Verdier ◽  
David Lepage ◽  
Arnaud Prébé ◽  
David Aymé-Perrot ◽  
...  
Keyword(s):  
Electrochemical Properties ◽  
Polymer Electrolytes ◽  
Ring Opening ◽  
Lithium Salt ◽  
Ring Opening Polymerization ◽  
Solid Polymer Electrolytes ◽  
Solid Polymer ◽  
Polymerization Reaction ◽  
Epoxide Ring ◽  
Epoxide Ring Opening

Solid polymer electrolytes have been widely proposed for use in all solid-state lithium batteries. Advantages of polymer electrolytes over liquid and ceramic electrolytes include their flexibility, tunability and easy processability. An additional benefit of using some types of polymers for electrolytes is that they can be processed without the use of solvents. An example of polymers that are compatible with solvent-free processing is epoxide-containing precursors that can form films via the lithium salt-catalyzed epoxide ring opening polymerization reaction. Many polymers with epoxide functional groups are liquid under ambient conditions and can be used to directly dissolve lithium salts, allowing the reaction to be performed in a single reaction vessel under mild conditions. The existence of a variety of epoxide-containing polymers opens the possibility for significant customization of the resultant films. This review discusses several varieties of epoxide-based polymer electrolytes (polyethylene, silicone-based, amine and plasticizer-containing) and to compare them based on their thermal and electrochemical properties.

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