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Synfacts 2006(7): 0633-0633  
DOI: 10.1055/s-2006-941825
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of SK&F 104353

Contributor(s): Philip Kocienski
V. K. Aggarwal*, J. P. H. Charmant, D. Fuentes, J. N. Harvey, G. Hynd, D. Ohara, W. Picoul, R. Robiette, C. Smith, J.-L. Vasse, C. L. Winn
Bristol University, UK
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

Good yields, high trans-selectivity and high enantioselectivities are the hallmarks of a synthesis of glycidic amides that have been applied to the synthesis of SK&F 104353, a leuko-triene D4 inhibitor with potential for the treatment of bronchial asthma. A previous synthesis achieved asymmetric epoxidation using a Julia-Colonna epoxidation of an α,β-unsaturated ketone with a polyleucine catalyst; see: I. Lantos et al. J. Org. Chem. 1993, 58, 6247-6254.