Arboreol

Arboreol is an epoxylignan.

Arboreol
Names
IUPAC name
(1R,4R,6aR)-1,4-Bis(1,3-benzodioxol-5-yl)dihydro-1H,3H-furo[3,4-c]furan-1,6a(6H)-diol
Other names
(7β,7'α,8α,8'α)-3,4:3',4'-bis(methylenedioxy)-7,9':7',9-diepoxylignane-7,8-diol
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C20H18O8/c21-19-8-23-18(11-1-3-14-16(5-11)26-9-24-14)13(19)7-28-20(19,22)12-2-4-15-17(6-12)27-10-25-15/h1-6,13,18,21-22H,7-10H2/t13-,18-,19-,20+/m1/s1
    Key: WQZHIPWFEKLEJM-AQWZQNETSA-N
  • O[C@@]43CO[C@H](C4CO[C@]3(O)c1ccc2OCOc2c1)c5ccc6OCOc6c5
Properties
C20H18O8
Molar mass 386.35 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Arboreol can be transformed by acid catalysis into gmelanone.[2]

References
  1. Buckingham, John (2 December 1993). Dictionary of Natural Products. CRC Press. p. 481. ISBN 978-0-412-46620-5.
  2. Acid catalysed rearrangements of arboreol: A biomimetic synthesis of gmelanone. L. Ramachandra Row and Reveru Ventkateswarlu, Tetrahedron Letters, 1980, Volume 21, Issue 30, Pages 2919–2922, doi:10.1016/S0040-4039(00)78645-X
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