Novel Stereoselective Syntheses of (+)-Streptol and (−)-1-epi-Streptol Starting from Naturally Abundant (−)-Shikimic Acid

Autor: Yun-Gang He, Wen-Jing Xie, Shi-Ling Liu, Xiao-Xin Shi, Yong-Kang Huang, Xing-Liang Zhu, Yong-Qiang Luo, Lei Wang
Rok vydání: 2021
Předmět:
Zdroj: ACS Omega, Vol 6, Iss 26, Pp 17103-17112 (2021)
ISSN: 2470-1343
DOI: 10.1021/acsomega.1c02502
Popis: Novel highly stereoselective syntheses of (+)-streptol and (-)-1-epi-streptol starting from naturally abundant (-)-shikimic acid were described in this article. (-)-Shikimic acid was first converted to the common key intermediate by 11 steps in 40% yield. It was then converted to (+)-streptol by three steps in 72% yield, and it was also converted to (-)-1-epi-streptol by one step in 90% yield. In summary, (+)-streptol and (-)-1-epi-streptol were synthesized from (-)-shikimic acid by 14 and 12 steps in 29 and 36% overall yields, respectively.
Databáze: OpenAIRE