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Efficient and Highly Stereoselective Syntheses of (+)-proto-Quercitol and (−)-gala-Quercitol Starting from the Naturally Abundant (−)-Shikimic Acid
- Source :
- ACS Omega, Vol 5, Iss 4, Pp 1813-1821 (2020), ACS Omega
- Publication Year :
- 2020
- Publisher :
- American Chemical Society, 2020.
-
Abstract
- Efficient and highly stereoselective syntheses of (+)-proto-quercitol and (-)-gala-quercitol starting from the naturally abundant (-)-shikimic acid were described in this article. (-)-Shikimic acid was first converted to the key intermediate by eight steps in 53% yield. It was then converted to (+)-proto-quercitol by three steps in 78% yield and was also converted to (-)-gala-quercitol by five steps in 63% yield. In summary, (+)-proto-quercitol and (-)-gala-quercitol were synthesized from (-)-shikimic acid by 11 and 13 steps in 41 and 33% overall yields, respectively.
Details
- Language :
- English
- ISSN :
- 24701343
- Volume :
- 5
- Issue :
- 4
- Database :
- OpenAIRE
- Journal :
- ACS Omega
- Accession number :
- edsair.doi.dedup.....48ea6255735614c1ea4f2841652e1c35