Enantioselective synthesis of pentacycloanammoxic acid.
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.
Mascitti
Vincent
V
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Corey
E J
EJ
D001421:Bacteria, Anaerobic / Q000737:chemistry / Q000378:metabolism; D018360:Crystallography, X-Ray; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D006090:Gram-Negative Bacteria / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004952:Esters; D011083:Polycyclic Compounds; C498357:pentacycloanammoxic acid methyl ester