A novel approach toward the synthesis of kendomycin: selective synthesis of a C-aryl glycoside as a single atropisomer.
[reaction: see text] A convergent and concise route to an advanced precursor 2b of kendomycin (1) has been developed by applying a S(N)1 ring cyclization as a key step. The resulting C-aryl glycoside was initially isolated as a rotameric mixture, but after MOM protection of the o-hydroxyl of the phenol, the conformation was frozen to the desired kendomycin-like atropisomer.
Pichlmair
Stefan
S
Institut für Organische Chemie, Währingerstrasse 38, A-1090 Wien, Austria.
Marques
Maria M B
MM
Green
Martin P
MP
Martin
Harry J
HJ
Mulzer
Johann
J
D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D017828:Rifabutin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D006027:Glycosides; C485395:kendomycin; D017828:Rifabutin