Oppolzer sultam directed aldol as a key step for the stereoselective syntheses of antitumor antibiotic belactosin C and its synthetic congeners.
[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.
Kumaraswamy
Gullapalli
G
Organic Division-III, Laboratory of X-ray crystallography, and NMR Division, Indian Institute of Chemical Technology, Hyderabad 500 007, India. gkswamy@iictnet.org
Padmaja
Mogilisetti
M
Markondaiah
Bekkam
B
Jena
Nivedita
N
Sridhar
Balasubramanian
B
Kiran
Marelli Udaya
MU
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
D000903:Antibiotics, Antineoplastic; D007783:Lactones; D010455:Peptides; D013449:Sulfonamides; C406054:belactosin C