A Novel Synthesis of Pterosin Z

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A Novel Synthesis of Pterosin Z

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1. A Novel Synthesis of Pterosin Z Synthesis of Fern Sesquiterpene Pterosin Z via a Novel Palladium-Catalyzed Route Farrell, R.; Kelleher, F.; Sheridan, H. J. Nat. Prod. 1996, 59 (4), 446-447.

2. Formula: C15 H20 O2 MW: 232.32 CAS RN: 34169-69-2 BP: 394.2±27.0 °C FP: 168.4±29.4 °C ?Hvap: 67.94±3.0 kJ/mol The Sesquiterpene Pterosin Z

3. Natural Sources of Pterosins Extracted from Bracken Fern (Pteridium aquilinum) as are other Pterosins Found in many Pteridophyta

4. Natural Sources of Pterosins Also found in various fungi, esp Basidiomycotina family

5. Fascination with Sesquiterpenes Many Pterosins exhibit pharmacological activity Smooth muscle relaxants Cytotoxic effects Ptaquilosides used to treat leukemia Presence in diverse evolutionary locations Taxonomic interest Phylogenetic interest

6. Pterosin Z from 6-bromoindan-1-one

7. Synthesis I Bromine is substituted with vinyl acetate by use of Heck's method of vinylic substitution using a Palladium catalyst

8. Synthesis II E and Z isomers are produced Reduced using Rhodium catalyzed hydrogenation Acetylpterosin Z is produced

9. Synthesis III Pterosin Z is obtained by deacylation of acetylpterosin Z

10. An indanone with a vinyl at position 6 is also obtained as a side reaction of the Heck substitution with increasing yield as temperature increases

11. Side Product This side product can be converted to Pterosin Z by protection of the carbonyl group followed by hydroboration

12. Other References Sheridan, H., N. Frankish, et al. Smooth muscle relaxant activity of pterosin Z and related compounds. Planta Medica. 1999. April 65(3): 271-272. Nilsson, P. Selectivity in Palladium and Enzyme Catalyzed Reactions. Dissertation. 2003. Uppsala University, Sweden.

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