Diastereomeric Resolution of a Racemic Biarylboronic Acid and Its Application to Divergent Asymmetric Total Syntheses of Some Axially Chiral Natural Products
- Authors
- Lee, Chun-Young; Cheon, Cheol-Hong
- Issue Date
- 18-2월-2016
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- axially chiral natural products; boronic acids; diastereomeric resolution; MIDA boronates; total synthesis
- Citation
- ADVANCED SYNTHESIS & CATALYSIS, v.358, no.4, pp.549 - 554
- Indexed
- SCIE
SCOPUS
- Journal Title
- ADVANCED SYNTHESIS & CATALYSIS
- Volume
- 358
- Number
- 4
- Start Page
- 549
- End Page
- 554
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/89500
- DOI
- 10.1002/adsc.201500798
- ISSN
- 1615-4150
- Abstract
- The asymmetric total syntheses of deshydroxytetramethylcupressuflavone and desmethylkotanin and the synthesis of a key intermediate in the previous synthesis of hibarimicinone are described using an axially chiral biarylboronic acid, prepared by the diastereomeric resolution of the corresponding rac-boronic acid, as a common intermediate. Conversion of the boronic acid moiety into either a hydrogen atom or a hydroxy group by protodeboronation or oxidation enabled us to complete the total syntheses of deshydroxytetramethylcupressuflavone and desmethylkotanin and synthesis of a key intermediate in the previous total synthesis of hibarimicinone, respectively.
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