(4R,4aR,6S,7S,7aS)‐6‐Hydroxy‐7‐hydroxymethyl‐4‐methylperhydrocyclopenta[c]pyran‐1‐one chloroform solvate from Valeriana laxiflora |
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Authors: | Smriti Khera Michael D Carducci Jian‐Qiao Gu Barbara N Timmermann |
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Abstract: | The structure of an iridolactone isolated from Valeriana laxiflora was established as (4R,4aR,6S,7S,7aS)‐6‐hydroxy‐7‐hydroxymethyl‐4‐methylperhydrocyclopentac]pyran‐1‐one chloroform solvate, C10H16O4·CHCl3. The two rings are cis‐fused. The δ‐lactone ring adopts a slightly twisted half‐chair conformation with approximate planarity of the lactone group and the cyclopentane ring adopts an envelope conformation. The hydroxy group, the hydroxymethyl group and the methyl group all have β orientations. The absolute configuration was determined using anomalous dispersion data enhanced by the adventitious inclusion of a chloroform solvent molecule. Hydrogen bonding, crystal packing and ring conformations are discussed in detail. |
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