Total synthesis of (-)-belactosin C and derivatives via double diastereoselective tandem mukaiyama aldol lactonizations.
[reaction: see text] The enantioselective synthesis of (-)-belactosin C and derivatives was accomplished in a concise manner employing the tandem, Mukaiyama aldol-lactonizaton (TMAL) process. One approach involved a distal double diastereoselective TMAL reaction with a dipeptide glyoxamide, whereas a second approach involved amide coupling of a dipeptide with a beta-lactone carboxylic acid, obtained via the TMAL process employing a chiral silyl ketene acetal. Notable improvements in diastereoselectivity were achieved in a proximal double diastereoselective TMAL process.
Cho
Sung Wook
SW
Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842-3012, USA.
Romo
Daniel
D
D000080:Acetals / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013453:Sulfonylurea Compounds / Q000737:chemistry
D000080:Acetals; D000447:Aldehydes; D004151:Dipeptides; D007659:Ketones; D007783:Lactones; D010455:Peptides; D013453:Sulfonylurea Compounds; C406054:belactosin C; C032160:glyoxamide; C116609:3-hydroxybutanal