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Issue 21, 2016
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Concise synthesis of calystegines B2 and B3via intramolecular Nozaki–Hiyama–Kishi reaction

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Abstract

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%).

Graphical abstract: Concise synthesis of calystegines B2 and B3via intramolecular Nozaki–Hiyama–Kishi reaction

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Publication details

The article was received on 02 Apr 2016, accepted on 28 Apr 2016 and first published on 03 May 2016


Article type: Paper
DOI: 10.1039/C6OB00697C
Citation: Org. Biomol. Chem., 2016,14, 4885-4896
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    Concise synthesis of calystegines B2 and B3via intramolecular Nozaki–Hiyama–Kishi reaction

    H. Wang, A. Kato, K. Kinami, Y. Li, G. W. J. Fleet and C. Yu, Org. Biomol. Chem., 2016, 14, 4885
    DOI: 10.1039/C6OB00697C

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