Efficient and Highly Stereoselective Syntheses of (+)-proto-Quercitol and (-)-gala-Quercitol Starting from the Naturally Abundant (-)-Shikimic Acid.

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.

SUBMITTER: Zhu XL 

PROVIDER: S-EPMC7003206 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature