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A New Stereocontrolled Total Synthesis of the Mast Cell Inhibitory Alkaloid (+)-Monanchorin

A New Stereocontrolled Total Synthesis of the Mast Cell Inhibitory Alkaloid (+)-Monanchorin. KarlJ.Hale* and Liping Wang . Org. Lett., 2014 , 16 (7), xxxx. Ailun Ma 2014. 4. 18. Author. Karl J. Hale. BSc University of London PhD University of London

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A New Stereocontrolled Total Synthesis of the Mast Cell Inhibitory Alkaloid (+)-Monanchorin

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  1. ANewStereocontrolledTotalSynthesisoftheMastCellInhibitoryAlkaloid(+)-MonanchorinANewStereocontrolledTotalSynthesisoftheMastCellInhibitoryAlkaloid(+)-Monanchorin KarlJ.Hale* andLipingWang. Org. Lett., 2014, 16 (7), xxxx Ailun Ma 2014. 4. 18

  2. Author Karl J. Hale • BSc University of London • PhD University of London • Chair of Organic and Medicinal Chemistry and Chemical Biology, Queen’s UniversityBelfast

  3. Introduction Isolation Isolated from the aqueous extract of the sponge Monanchora. Structure features A guanidine alkaloid with an unusual bicyclic skeleton, together with the known pentacyclic alkaloid crambescidin acid. Bioactivities Anti-cancer

  4. Retrosynthesis

  5. Initial Attempt at Preparing Aldehyde 4

  6. A New Total Synthesis of (+)-Monanchorin

  7. Conclusion They havedevelopedanewandfullystereocontrolledasymmetricsynthesisofthemastcellinhibitoryalkaloid,(+)-monanchorin,thatdeliversthismoleculeasitsTFAsaltinhigheeandhighoverallyield(7.2%,12steps).

  8. Thank you

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