Synthesis of Bafilomycin A1

F. Kleinbeck; E. M. Carreira

doi:10.1055/s-0029-1216670

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Synfacts 2009(6): 0585-0585
DOI: 10.1055/s-0029-1216670

Synthesis of Natural Products and Potential Drugs

Synthesis of Bafilomycin A₁

Contributor(s): Philip Kocienski, Arndt W. Schmidt
F. Kleinbeck, E. M. Carreira*
ETH Zürich, Switzerland

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Publikationsdatum:
25. Mai 2009 (online)

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Significance

Bafilomycin A₁ was isolated from a Streptomyces griseus sp. sulphurus culture and exhibits broad antibacterial and antifungal activity. In addition, it is a selective V-type ATPase inhibitor. The potency for the treatment of osteoporosis has been evaluated. The focal step of this synthesis is a diastereoselective alkynylation of aldehyde D followed by a formal transhydrogenation to create the C12-C13 double bond.