Multi-chelation approach towards natural product-like skeletons: one-pot access to a nitrogen-containing tetracyclic framework from AlaAla dipeptide.
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!
Vellaisamy
Kasipandi
K
Department of Chemistry, Indian Institute of Technology Madras, Chennai-600 036, India.
Napoleon
John Victor
JV
Venkatachalam
Ramkumar
R
Manheri
Muraleedharan Kannoth
MK
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
D001688:Biological Products; D002614:Chelating Agents; D004151:Dipeptides; D009584:Nitrogen; D001895:Boron; D000409:Alanine