Chemoenzymatic synthesis of carbasugars (+)-pericosines A-C from diverse aromatic cis-dihydrodiol precursors.
cis-Dihydrocatechols, derived from biological cis-dihydroxylation of methyl benzoate, iodobenzene and benzonitrile, using the microorganism Pseudomonas putida UV4, were converted into pericosines A, C, and B, respectively. This approach constitutes the shortest syntheses, to date, of these important natural products with densely packed functionalities.
Boyd
Derek R
DR
School of Chemistry and Chemical Engineering, Queen's University of Belfast, Belfast BT9 5AG, United Kingdom.
Sharma
Narain D
ND
Acaru
Carmen A
CA
Malone
John F
JF
O'Dowd
Colin R
CR
Allen
Christopher C R
CC
Stevenson
Paul J
PJ
D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry*; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D009281:Naphthalenes; C523077:methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate; C496389:pericosine B; C544052:pericosine C; C507866:trans-1,2-dihydro-1,2-naphthalenediol; D012765:Shikimic Acid