Total Synthesis and Configurational Validation of (+)-Violapyrone C
- Authors
- Lee, Jong Seok; Shin, Junho; Shin, Hee Jae; Lee, Hwa-Sun; Lee, Yeon-Ju; Lee, Hyi-Seung; Won, Hoshik
- Issue Date
- Jul-2014
- Publisher
- John Wiley & Sons Ltd.
- Keywords
- Total synthesis; Natural products; Oxygen heterocycles; Gold; Wittig reactions
- Citation
- European Journal of Organic Chemistry, v.2014, no.21, pp.4472 - 4476
- Indexed
- SCIE
SCOPUS
- Journal Title
- European Journal of Organic Chemistry
- Volume
- 2014
- Number
- 21
- Start Page
- 4472
- End Page
- 4476
- URI
- https://scholarworks.bwise.kr/erica/handle/2021.sw.erica/22424
- DOI
- 10.1002/ejoc.201402524
- ISSN
- 1434-193X
- 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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Collections - COLLEGE OF SCIENCE AND CONVERGENCE TECHNOLOGY > DEPARTMENT OF CHEMICAL AND MOLECULAR ENGINEERING > 1. Journal Articles
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