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Saudin

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Saudin
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • C1C2C3(O4(2(5(O3)COC(=O)5(CC4)C)C)OC1=O)C6=COC=C6
Properties
Chemical formula C20H22O7
Molar mass 374.389 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Saudin is a diterpenoid first isolated from the African flowering plant Cluytia richardiana.

Saudin has shown a hypoglycemic effect in an rodent model experiment.

Because of the unusual chemical structure and its potential biological activity, there has been research aimed at its total synthesis.

References

  1. Mossa, Jaber S.; Cassady, John M.; Antoun, Mikhail D.; Byrn, Stephen R.; McKenzie, Ann T.; Kozlowski, John F.; Main, P. (1985). "Saudin, a hypoglycemic diterpenoid, with a novel 6,7-seco-labdane carbon skeleton, from Cluytia richardiana". The Journal of Organic Chemistry. 50 (6): 916–918. doi:10.1021/jo00206a050.
  2. Mossa, J. S.; El-Denshary, E. S. M.; Hindawi, R.; Ageel, A. M. (1988). "The Hypoglycaemic Effect of Saudin". International Journal of Crude Drug Research. 26 (2): 81–87. doi:10.3109/13880208809053897.
  3. Boeckman, Robert K.; Rosario Ferreira, Maria Rico del; Mitchell, Lorna H.; Shao, Pengcheng; Neeb, Michael J.; Fang, Yue (2011). "Studies culminating in the total synthesis and determination of the absolute configuration of (−)-saudin". Tetrahedron. 67 (51): 9787–9808. doi:10.1016/j.tet.2011.09.067. PMC 3328808. PMID 22523435.
  4. Labadie, Guillermo R.; Cravero, Raquel M.; González-Sierra, Manuel (1996). "Studies Toward the Total Synthesis of Saudine : Simple and Stereoselective Synthesis of a Model Caged Ketal Backbone". Synthetic Communications. 26 (24): 4671–4684. doi:10.1080/00397919608004793.
  5. Boeckman, Robert K.; Del Rosario Rico Ferreira, Maria; Mitchell, Lorna H.; Shao, Pengcheng (2002). "An Enantioselective Total Synthesis of (+)- and (−)-Saudin. Determination of the Absolute Configuration". Journal of the American Chemical Society. 124 (2): 190–191. doi:10.1021/ja017194i. PMID 11782168.
  6. Tambar, Uttam K.; Kano, Taichi; Stoltz, Brian M. (2005). "Progress toward the Total Synthesis of Saudin: Development of a Tandem Stille-Oxa-Electrocyclization Reaction" (PDF). Organic Letters. 7 (12): 2413–2416. doi:10.1021/ol050705b. PMID 15932211.
  7. Tambar, U. K.; Kano, T.; Zepernick, J. F.; Stoltz, B. M. (2008). "Convergent and diastereoselective synthesis of the polycyclic pyran core of saudin" (PDF). The Journal of Organic Chemistry. 71 (22): 8357–64. doi:10.1021/jo061236+. PMID 17064005. S2CID 21506656.


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