Total Synthesis and Configurational Validation of (+)-Violapyrone C
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Title
- Total Synthesis and Configurational Validation of (+)-Violapyrone C
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Author(s)
- Lee, Jong Seok; Shin, Junho; Shin, Hee Jae; Lee, Hwa-Sun; Lee, Yeon-Ju; Lee, Hyi-Seung; Won, Hoshik
- KIOST Author(s)
- Lee, Jong Seok(이종석); Shin, Hee Jae(신희재); Lee, Hwa Sun(이화선); Lee, Yeon Ju(이연주); Lee, Hyi Seung(이희승)
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Alternative Author(s)
- 이종석; 신준호; 신희재; 이화선; 이연주; 이희승
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Publication Year
- 2014-07
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Abstract
- Gold(I)-catalyzed intramolecular 6-endo-dig cyclization of tert-butyl ynoates afforded alpha-pyrone cores of violapyrones. Moreover, this reaction was successfully applied to the stereospecific syntheses of (+)- and (-)-violapyrone C, which allowed the absolute configuration of natural (+)-violapyrone C to be assigned by comparison of the optical rotations. This first total synthesis, which proceeded in 22% yield over 10 steps from (S)-(-)-2-methylbutanol, features silver(I) oxide promoted monobenzylation of 1,4-butanediol, Wittig ole-fination, Claisen condensation, Corey-Fuchs reaction, and gold(I)-catalyzed alpha-pyrone synthesis.
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ISSN
- 1434-193X
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URI
- https://sciwatch.kiost.ac.kr/handle/2020.kiost/2780
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DOI
- 10.1002/ejoc.201402524
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Bibliographic Citation
- EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no.21, pp.4472 - 4476, 2014
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Publisher
- WILEY-V C H VERLAG GMBH
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Subject
- 1ST TOTAL-SYNTHESIS; REGIOSELECTIVE SYNTHESIS; 3-SUBSTITUTED ISOCOUMARINS; COUPLING REACTIONS; GOLD; DERIVATIVES; ACIDS; CYCLIZATION; HETEROCYCLES; SUBSTITUENT
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Keywords
- Total synthesis; Natural products; Oxygen heterocycles; Gold; Wittig reactions
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Type
- Article
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Language
- English
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Document Type
- Article
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