title: Total synthesis of (-)-nakadomarin A.
abstract: The convergent synthesis of the polycyclic alkaloid (-)-nakadomarin A (1) is reported. The synthesis plan identified macrocyclic lactam 4 as one of the important synthons (eight steps). The other synthon (five steps) was bicyclo[6.3.0] lactam 5 containing a single stereocenter that controlled all of the subsequent stereochemistry during the assembly process. A silyl triflate-promoted cascade of 4 and 5 was used to assemble the bulk of the alkaloid skeleton with the exception of the C5-C6 bond. The nakadomarin synthesis was then completed in one additional step.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.
authors.forename: Simone
authors.initials: S
authors.lastname: Bonazzi
authors.forename: Bichu
authors.initials: B
authors.lastname: Cheng
authors.forename: Joseph S
authors.initials: JS
authors.lastname: Wzorek
authors.forename: David A
authors.initials: DA
authors.lastname: Evans
mesh_terms: D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D002243:Carbolines; C476640:nakadomarin A