Total synthesis of (+/-)-pentacycloanammoxic acid.
The first total synthesis of (+/-)-pentacycloanammoxic acid/methyl ester (1), an unusual naturally occurring fatty acid from Candidatus Brocadia anammoxidans, has been accomplished by the sequence of reactions shown in Scheme 1. The C20-structure of 1 was assembled with stereocontrol from three building blocks: cyclooctatetraene, 2-cyclopentenone, and 7-bromoheptanoic acid. The synthesis of 1 confirms the proposed structure of 1. The mode of biosynthesis and absolute configuration have yet to be clarified.
Mascitti
Vincent
V
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Corey
E J
EJ
D001421:Bacteria, Anaerobic / Q000737:chemistry; D018360:Crystallography, X-Ray; D003503:Cyclobutanes / Q000138:chemical synthesis*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D003503:Cyclobutanes; D004952:Esters; D011083:Polycyclic Compounds; D000644:Quaternary Ammonium Compounds; C498357:pentacycloanammoxic acid methyl ester