Concise synthesis of calystegines B2 and B3via intramolecular Nozaki–Hiyama–Kishi reaction
- The key step in the concise syntheses of calystegine B2 and its C-2 epimer calystegine B3 was the construction of cycloheptanone 8via an intramolecular Nozaki-Hiyama-Kishi (NHK) reaction of 9, an aldehyde containing a Z-vinyl iodide. Vinyl iodide 9 was obtained by the Stork olefination of aldehyde 10, derived from carbohydrate starting materials. Calystegines B2 (3) and B3 (4) were synthesized from d-xylose and l-arabinose derivatives respectively in 11 steps in excellent overall yields (27% and 19%).
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+ Ministry of Science and Technology of P. R. China More from this funder
+ National Science and Technology Major Projects More from this funder
“Major New Drugs Innovation and Development” (2013ZX09508104)
Chinese Academy of Science More from this funderExpand funders...
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- © the Author(s). This journal is © The Royal Society of Chemistry 2017.
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