Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides
Abstract: A convergent, nine‐step (LLS), enantioselective synthesis of α‐cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with a chiral sulfur ylide; b) a bioinspired (3+2)‐cycloaddition of the aziridine onto an alkene; and c) installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/N−O cleavage of a bromoisoxazole.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides ; volume:130 ; number:5 ; year:2018 ; pages:1360-1364 ; extent:5
Angewandte Chemie ; 130, Heft 5 (2018), 1360-1364 (gesamt 5)
- Creator
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Zhurakovskyi, Oleksandr
Türkmen, Yunus E.
Löffler, Lorenz E.
Moorthie, Vijayalakshmi A.
Chen, C. Chun
Shaw, Michael A.
Crimmin, Mark R.
Ferrara, Marco
Ahmad, Mushtaq
Ostovar, Mehrnoosh
Matlock, Johnathan V.
Aggarwal, Varinder K.
- DOI
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10.1002/ange.201712065
- URN
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urn:nbn:de:101:1-2022090109152981023758
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:37 AM CEST
Data provider
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Associated
- Zhurakovskyi, Oleksandr
- Türkmen, Yunus E.
- Löffler, Lorenz E.
- Moorthie, Vijayalakshmi A.
- Chen, C. Chun
- Shaw, Michael A.
- Crimmin, Mark R.
- Ferrara, Marco
- Ahmad, Mushtaq
- Ostovar, Mehrnoosh
- Matlock, Johnathan V.
- Aggarwal, Varinder K.
Other Objects (12)
Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides
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Gold‐Catalyzed Cycloisomerization of Sulfur Ylides to Dihydrobenzothiepines
Catalytic Enantioselective (3+2) Cycloaddition of N‐Metalated Azomethine Ylides
Enantioselective S−H Insertion Reactions of α‐Carbonyl Sulfoxonium Ylides
Enantioselective S−H Insertion Reactions of α‐Carbonyl Sulfoxonium Ylides
Copper-Catalyzed Asymmetric [4+1] Annulation of Sulfur Ylides
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Catalyst‐ and Substrate‐Dependent Chemodivergent Reactivity of Stabilised Sulfur Ylides with Salicylaldehydes
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Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides
Novel dianionic sulfur ylides and related compounds
Novel dianionic sulfur ylides and related compounds
Sulfur-Based Ylides in Transition-Metal-Catalysed Processes
Gold‐Catalyzed Cycloisomerization of Sulfur Ylides to Dihydrobenzothiepines
Catalytic Enantioselective (3+2) Cycloaddition of N‐Metalated Azomethine Ylides
Enantioselective S−H Insertion Reactions of α‐Carbonyl Sulfoxonium Ylides
Enantioselective S−H Insertion Reactions of α‐Carbonyl Sulfoxonium Ylides
Copper-Catalyzed Asymmetric [4+1] Annulation of Sulfur Ylides
Syntheses and electron density determination of novel polyimido sulfur ylides
Catalyst‐ and Substrate‐Dependent Chemodivergent Reactivity of Stabilised Sulfur Ylides with Salicylaldehydes
Phosphorus ylides, sulfur ylides, and related carbanions as reference nucleophiles for the quantification of the electrophilic reactivities of aldehydes, imines, and enones
Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides
Novel dianionic sulfur ylides and related compounds
Novel dianionic sulfur ylides and related compounds
Sulfur-Based Ylides in Transition-Metal-Catalysed Processes
Gold‐Catalyzed Cycloisomerization of Sulfur Ylides to Dihydrobenzothiepines
Catalytic Enantioselective (3+2) Cycloaddition of N‐Metalated Azomethine Ylides
Enantioselective S−H Insertion Reactions of α‐Carbonyl Sulfoxonium Ylides
Enantioselective S−H Insertion Reactions of α‐Carbonyl Sulfoxonium Ylides
Copper-Catalyzed Asymmetric [4+1] Annulation of Sulfur Ylides
Syntheses and electron density determination of novel polyimido sulfur ylides
Catalyst‐ and Substrate‐Dependent Chemodivergent Reactivity of Stabilised Sulfur Ylides with Salicylaldehydes