Synthesis of L-kedarosamine in protected form and its efficient incorporation into an advanced intermediate to kedarcidin chromophore.
An efficient route to the complex L-kedarosamine alpha-glycosidic ether 2, a synthetic precursor to kedarcidin chromophore, is described. Central to the route, which is suitable for the preparation of multigram amounts of material, is a short synthetic sequence from D-threonine to protected L-kedarosamine derivatives and methodology for their alpha-selective coupling with appropriate hydroxyl acceptors.
Ren
Feng
F
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.
Hogan
Philip C
PC
Anderson
Alan J
AJ
Myers
Andrew G
AG
D000480:Alkynes / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D003516:Cycloparaffins / Q000138:chemical synthesis* / Q000737:chemistry; D053281:Enediynes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013912:Threonine / Q000737:chemistry
D000480:Alkynes; D000588:Amines; D003516:Cycloparaffins; D053281:Enediynes; C520456:L-kedarosamine; D009281:Naphthalenes; D011714:Pyrans; C080542:kedarcidin chromophore; D013912:Threonine