title: A macrocyclic approach to tetracycline natural products. Investigation of transannular alkylations and Michael additions.
abstract: A new approach to the tetracycline core structure is presented. The pivotal intermediate is identified as macrocycle III. The two interior bonds (C4a-C12a and C5a-C11a) are to be constructed through sequential transannular Michael additions (III-II) and compression-promoted transannular isoxazole alkylations from intermediate II.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
authors.forename: Joseph S
authors.initials: JS
authors.lastname: Wzorek
authors.forename: Thomas F
authors.initials: TF
authors.lastname: Knöpfel
authors.forename: Ioannis
authors.initials: I
authors.lastname: Sapountzis
authors.forename: David A
authors.initials: DA
authors.lastname: Evans
mesh_terms: D000478:Alkylation; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003500:Cyclization; D007555:Isoxazoles / Q000737:chemistry*; D015394:Molecular Structure; D013752:Tetracycline / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D001688:Biological Products; D007555:Isoxazoles; D013752:Tetracycline