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

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.

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

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>

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