Synthesis of the C1-C21 (C1'-C21') fragment of the dimeric polyketide natural product SCH 351448.
[structure: see text] A convergent, stereoselective assembly of the C1-C21 (C1'-C21') fragment of SCH 351448, a 28-membered bis-lactone natural product, has been developed. A highly efficient approach to this fragment assembles 75% of the carbon skeleton and all the stereochemical elements present in the natural product. In addition, an interesting boron ligand effect on the diastereoselectivity of a key aldol reaction with methyl ketone-derived enolborinates is reported.
Bhattacharjee
Ashoke
A
Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas, Dallas, Texas 75390-9038, USA.
Soltani
Omid
O
De Brabander
Jef K
JK
D000924:Anticholesteremic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008847:Micromonospora / Q000737:chemistry; D008968:Molecular Conformation
D000924:Anticholesteremic Agents; D007202:Indicators and Reagents; D007783:Lactones; C451479:SCH 351448