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. 2021 Jun 23;6(26):17103-17112.
doi: 10.1021/acsomega.1c02502. eCollection 2021 Jul 6.

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

Xing-Liang Zhu  1 , Yong-Qiang Luo  1 , Lei Wang  1 , Yong-Kang Huang  1 , Yun-Gang He  1 , Wen-Jing Xie  1 , Shi-Ling Liu  2 , Xiao-Xin Shi  1
Affiliations

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

Xing-Liang Zhu et al. ACS Omega. .

Abstract

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.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Three related compounds.
Scheme 1
Scheme 1. Total Syntheses of (+)-Streptol 1 and (−)-1-epi-Streptol 2 Starting from (−)-Shikimic Acid
Figure 2
Figure 2
1H–1H COSY and 1H–1H NOESY spectra of 9.
Figure 3
Figure 3
Chemoselective reduction of 9 with NaBH4.
See this image and copyright information in PMC

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