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Synfacts 2014; 10(9): 0894
DOI: 10.1055/s-0034-1378569
DOI: 10.1055/s-0034-1378569
Synthesis of Natural Products and Potential Drugs
Synthesis of γ-Secretase Modulator SPI-1865
Fuller NO, * Hubbs JL, Austin WF, Shen R, Ives J, Osswald G, Bronk BS. Satori Pharmaceuticals, Cambridge, USA and Carbogen-Amcis AG, Aarau, Switzerland
Optimization of a Kilogram-Scale Synthesis of a Potent Cycloartenol Triterpenoid-Derived γ-Secretase Modulator.
Org. Process Res. Dev. 2014;
18: 683-692
Optimization of a Kilogram-Scale Synthesis of a Potent Cycloartenol Triterpenoid-Derived γ-Secretase Modulator.
Org. Process Res. Dev. 2014;
18: 683-692
Further Information
Publication History
Publication Date:
18 August 2014 (online)
Significance
SPI-1865 is a γ-secretase modulator that is of interest for the treatment of Alzheimer’s disease. Kilogram batches of the API were generated by the route depicted, which features (1) a highly stereoselective ZrCl4-catalyzed rearrangement of A to the ketone B and (2) selective O-ethylation of the C24 hydroxyl group in triol G.
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Comment
For a multikilogram-scale production of the diastereoisomeric cycloartenol triterpenoid glycoside A from Actaea racemosa (black cohosh), see: R. Shen et al. Org. Process Res. Dev. 2014, 18, 676.
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