A convergent approach toward the C1-C11 subunit of phoslactomycins and formal synthesis of phoslactomycin B.
The preparation of the C1-C11 subunit of phoslactomycins, and a formal synthesis of phoslactomycin B, were achieved by a convergent strategy involving the chelation-controlled addition of an alkynyl Grignard reagent to an alpha-alkoxy ketone. Catalytic enantioselective reductions of acetylenic ketones and a [2,3]-Wittig rearrangement were utilized as key steps to control the configuration of the C4, C5, and C9 stereocenters.
Druais
Valérie
V
Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Hall
Michael J
MJ
Corsi
Camilla
C
Wendeborn
Sebastian V
SV
Meyer
Christophe
C
Cossy
Janine
J
D002384:Catalysis; D003300:Copper / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D004852:Epoxy Compounds; D007202:Indicators and Reagents; D007659:Ketones; D007783:Lactones; D009943:Organophosphorus Compounds; C060449:phoslactomycin B; D003300:Copper