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.
| Original language | English |
|---|---|
| Pages (from-to) | 549-554 |
| Number of pages | 6 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 358 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 2016 Feb 18 |
Bibliographical note
Funding Information:This work was supported by grants from the National Research Foundation of Korea (NRF) funded by the Korean Government (NRF-2013R1A1A1008434 and NRF- 2015R1D1A1A01057200). We are also thankful for an NRF grant (NRF-2014-011165, Center for New Directions in Organic Synthesis). Finally, C.-H.C. thanks the Posco TJ Park Foundation for their generous support.
Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Keywords
- MIDA boronates
- axially chiral natural products
- boronic acids
- diastereomeric resolution
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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