title: Oppolzer sultam directed aldol as a key step for the stereoselective syntheses of antitumor antibiotic belactosin C and its synthetic congeners.
abstract: [reaction: see text] An efficient protocol has been developed using D-(2R)-Oppolzer sultam as a chiral auxiliary for generating anti/syn diastereomers with high enantiopurity and utilized in the efficient synthesis of natural product belactosin C and their synthetic congeners. It has been observed that a variation in the stoichiometry of the Lewis acid led to a difference in anti/syn selectivity.
authors.affiliation: Organic Division-III, Laboratory of X-ray crystallography, and NMR Division, Indian Institute of Chemical Technology, Hyderabad 500 007, India. gkswamy@iictnet.org
authors.forename: Gullapalli
authors.initials: G
authors.lastname: Kumaraswamy
authors.forename: Mogilisetti
authors.initials: M
authors.lastname: Padmaja
authors.forename: Bekkam
authors.initials: B
authors.lastname: Markondaiah
authors.forename: Nivedita
authors.initials: N
authors.lastname: Jena
authors.forename: Balasubramanian
authors.initials: B
authors.lastname: Sridhar
authors.forename: Marelli Udaya
authors.initials: MU
authors.lastname: Kiran
mesh_terms: D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000903:Antibiotics, Antineoplastic; D007783:Lactones; D010455:Peptides; D013449:Sulfonamides; C406054:belactosin C