title: A radical cyclization approach to the formal total syntheses of platencin.
abstract: Two different strategies leading to formal total syntheses of platencin are described. The first strategy involving Claisen rearrangement and radical cyclization provides a rapid access to the core structure of platencin, and also use minimum protective-group operations. The second strategy, a protecting group-free route, utilizes a 6-exo-trig radical cyclization and aldol condensation as key steps leading to the formal synthesis of platencin.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076, India.
authors.forename: Kalanidhi
authors.initials: K
authors.lastname: Palanichamy
authors.forename: Ayyagari V
authors.initials: AV
authors.lastname: Subrahmanyam
authors.forename: Krishna P
authors.initials: KP
authors.lastname: Kaliappan
mesh_terms: D015099:3-Oxoacyl-(Acyl-Carrier-Protein) Synthase; D000123:Acetyltransferases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D000627:Aminophenols / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects / Q000201:enzymology; D001424:Bacterial Infections / Q000188:drug therapy / Q000382:microbiology; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D003500:Cyclization; D055808:Drug Discovery; D029968:Escherichia coli Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D054889:Fatty Acid Synthase, Type II / Q000037:antagonists & inhibitors / Q000378:metabolism; D005227:Fatty Acids / Q000378:metabolism; D005609:Free Radicals / Q000737:chemistry; D006801:Humans; D050356:Lipid Metabolism / Q000187:drug effects; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000627:Aminophenols; D000900:Anti-Bacterial Agents; D029968:Escherichia coli Proteins; D005227:Fatty Acids; D005609:Free Radicals; D011083:Polycyclic Compounds; D000123:Acetyltransferases; C557158:fabH protein, E coli; D015099:3-Oxoacyl-(Acyl-Carrier-Protein) Synthase; D054889:Fatty Acid Synthase, Type II; C520340:platencin