Enantioselective synthesis of pentacycloanammoxic acid

Journal of the American Chemical Society
Vincent Mascitti, E J Corey

Abstract

A highly effective enantioselective synthesis of pentacycloanammoxic acid (1), an unusual naturally occurring fatty acid from Candidatus Brocadia anammoxidans, has been accomplished. The C20-structure of 1 was assembled with stereocontrol from four building blocks, cyclobutene, 2-cyclopentenone, the chiral silylcyclopentenone 6, and 7-bromoheptanoic acid. Both 1 and its enantiomer are now available in quantities that should facilitate future studies on the mode of biosynthesis which appears to be unprecedented.

References

Oct 18, 2002·Nature·Edward F DeLong
Dec 2, 2004·Journal of the American Chemical Society·Vincent Mascitti, E J Corey

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