Chemistry:Steganacin

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Steganacin
Steganacin.svg
(−)-Steganacin
Names
Preferred IUPAC name
(3aS,14S,14aS)-6,7,8-Trimethoxy-3-oxo-1,3,3a,4,14,14a-hexahydro-11H-benzo[3,4]furo[3′,4′:6,7]cycloocta[1,2-f][1,3]benzodioxol-14-yl acetate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
Properties
C24H24O9
Molar mass 456.44 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

Steganacin is an dibenzocyclooctadiene lactone, an unusual type of lignan.[1] It exhibits some antileukemic properties. It has been isolated from Steganotaenia araliacea.[2] (−)-Steganacin is the natural form.[3]

Notes

  1. Umezawa, Toshiaki (2003). "Diversity in lignan biosynthesis". Phytochemistry Reviews 2 (3): 371–390. doi:10.1023/B:PHYT.0000045487.02836.32. Bibcode2003PChRv...2..371U. 
  2. Kupchan, SM; Britton, RW; Ziegler, MF; Gilmore, CJ; Restivo, RJ; Bryan, RF (21 February 1973). "Steganacin and steganangin, novel antileukemic lignan lactones from Steganotaenia araliacea.". Journal of the American Chemical Society 95 (4): 1335–6. doi:10.1021/ja00785a054. PMID 4687687. 
  3. Augros, David; Yalcouye, Boubacar; Choppin, Sabine; Chessé, Matthieu; Panossian, Armen; Leroux, Frédéric R. (18 January 2017). "Transition-Metal-Free Synthesis of a Known Intermediate in the Formal Synthesis of (-)-Steganacin: Transition-Metal-Free Synthesis of a Known Intermediate in the Formal Synthesis of (-)-Steganacin". European Journal of Organic Chemistry 2017 (3): 497–503. doi:10.1002/ejoc.201601239. https://hal.archives-ouvertes.fr/hal-02105793/file/EJOC_Biaryls_revised.pdf.