Gmelanone

Gmelanone is a lignan found in the heartwood of Gmelina arborea.[1] Arboreol can be transformed by acid catalysis into gmelanone.[2]

Gmelanone

Names
IUPAC name (1R,2S,5S)-2,5-Bis(1,3-benzodioxol-5-yl)-3,6-dioxabicyclo[3.2.1]octan-8-one
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	10308036
PubChem CID	21722946
InChI InChI=1S/C20H16O7/c21-19-13-7-27-20(19,12-2-4-15-17(6-12)26-10-24-15)8-22-18(13)11-1-3-14-16(5-11)25-9-23-14/h1-6,13,18H,7-10H2/t13-,18-,20-/m1/s1 Key: NNFGXXXVGRYOSF-CFSSXQINSA-N
SMILES O=C4[C@@H]1CO[C@]4(CO[C@@H]1c2ccc3OCOc3c2)c5ccc6OCOc6c5
Properties
Chemical formula	C20H16O7
Molar mass	368.341 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References

1. Anjaneyulu, A.S.R.; Rao, A.Madhusudhana; Rao, V.Kameswara; Row, L.Ramachandra; Pelter, Andrew; Ward, Robert S. (1977). "Novel hydroxy lignans from the heartwood of gmelina arborea". Tetrahedron. 33: 133–143. doi:10.1016/0040-4020(77)80444-4.
2. Ramachandra Row, L.; Ventkateswarlu, Reveru; Pelter, Andrew; Ward, Robert S. (1980). "Acid catalysed rearrangements of arboreol: A biomimetic synthesis of gmelanone". Tetrahedron Letters. 21 (30): 2919. doi:10.1016/S0040-4039(00)78645-X.