Saudin

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Saudin
Saudin.svg
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C20H22O7/c1-11-13-8-18(12-4-7-23-9-12)26-19-10-24-15(22)16(19,2)5-6-20(27-18,17(13,19)3)25-14(11)21/h4,7,9,11,13H,5-6,8,10H2,1-3H3/t11-,13?,16-,17-,18-,19-,20+/m1/s1
    Key: MIZCOUBLUGPQEO-UHMNIBCTSA-N
  • C[C@@H]1C2C[C@@]3(O[C@@]4([C@]2([C@@]5(O3)COC(=O)[C@]5(CC4)C)C)OC1=O)C6=COC=C6
Properties
C20H22O7
Molar mass 374.389 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Saudin is a diterpenoid first isolated from the African flowering plant Cluytia richardiana . [1]

Saudin has shown a hypoglycemic effect in an rodent model experiment. [2]

Because of the unusual chemical structure and its potential biological activity, there has been research aimed at its total synthesis. [3] [4] [5] [6] [7]

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. Bibcode:2002JAChS.124..190B. 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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