title: Multi-chelation approach towards natural product-like skeletons: one-pot access to a nitrogen-containing tetracyclic framework from AlaAla dipeptide.
abstract: Reductive transformation of the dipeptide BocAlaAlaOMe to a complex, internally charge-stabilized, natural product-like skeleton in one synthetic step is discussed. Stepwise replacement of the B-H bonds in borane by B-N or B-O resulted in incorporation of three boron atoms in a tetracyclic framework whereby one is stereogenic!
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai-600 036, India.
authors.forename: Kasipandi
authors.initials: K
authors.lastname: Vellaisamy
authors.forename: John Victor
authors.initials: JV
authors.lastname: Napoleon
authors.forename: Ramkumar
authors.initials: R
authors.lastname: Venkatachalam
authors.forename: Muraleedharan Kannoth
authors.initials: MK
authors.lastname: Manheri
mesh_terms: D000409:Alanine / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D001895:Boron; D002614:Chelating Agents / Q000737:chemistry*; D003500:Cyclization; D004151:Dipeptides / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry
chemical_list: D001688:Biological Products; D002614:Chelating Agents; D004151:Dipeptides; D009584:Nitrogen; D001895:Boron; D000409:Alanine