Construction of a C(30−38) Dioxabicyclo[3.2.1]octane Subtarget for (+)-Sorangicin A, Exploiting a Regio- and Stereocontrolled Acid-Catalyzed Epoxide Ring Opening

2004 ◽  
Vol 6 (9) ◽  
pp. 1477-1480 ◽  
Author(s):  
Amos B. Smith ◽  
Richard J. Fox
Keyword(s):  
Ring Opening ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Acid Catalyzed ◽  
Sorangicin A ◽  
C 30

ChemInform Abstract: Non-Lewis Acid Catalyzed Epoxide Ring Opening with Amino Acid Esters.

ChemInform ◽  
2009 ◽  
Vol 40 (40) ◽  
Author(s):  
Christine Philippe ◽  
Thierry Milcent ◽  
Benoit Crousse ◽  
Daniele Bonnet-Delpon
Keyword(s):  
Amino Acid ◽  
Lewis Acid ◽  
Ring Opening ◽  
Epoxide Ring ◽  
Amino Acid Esters ◽  
Epoxide Ring Opening ◽  
Acid Catalyzed ◽  
Acid Esters

An Acid-Catalyzed Epoxide Ring-Opening/Transesterification Cascade Cyclization to Diastereoselective Syntheses of (±)-β-Noscapine and (±)-β-Hydrastine

2019 ◽  
Vol 21 (17) ◽  
pp. 7149-7153 ◽  
Author(s):  
Jihui Li ◽  
Yongxiang Liu ◽  
Xinjing Song ◽  
Tianxiao Wu ◽  
Jiaxin Meng ◽  
...  
Keyword(s):  
Ring Opening ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Cascade Cyclization ◽  
Acid Catalyzed

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.

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