Total Synthesis and Configurational Validation of (+)-Violapyrone C SCIE SCOPUS

Cited 13 time in WEB OF SCIENCE Cited 15 time in Scopus
Title
Total Synthesis and Configurational Validation of (+)-Violapyrone C
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 Soo(이종수)Lee, Hwa Sun(이화선)Lee, Yeon Ju(이연주)Lee, Hyi Seung(이희승)
Publication Year
2014-07
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.
ISSN
1434-193X
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/2780
DOI
10.1002/ejoc.201402524
Bibliographic Citation
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no.21, pp.4472 - 4476, 2014
Publisher
WILEY-V C H VERLAG GMBH
Subject
1ST TOTAL-SYNTHESIS; REGIOSELECTIVE SYNTHESIS; 3-SUBSTITUTED ISOCOUMARINS; COUPLING REACTIONS; GOLD; DERIVATIVES; ACIDS; CYCLIZATION; HETEROCYCLES; SUBSTITUENT
Keywords
Total synthesis; Natural products; Oxygen heterocycles; Gold; Wittig reactions
Type
Article
Language
English
Document Type
Article
Publisher
WILEY-V C H VERLAG GMBH
Related Researcher
Research Interests

Marine Natural Products,Organic Chemistry,해양천연물,유기화학

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