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

[Image: see text] 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.