Efficient and stereoselective access to the polyol fragment C9-C16 of ansamycin antibiotics.
Efficient synthesis of the fragment C9-C16 bearing the anti,syn stereotriad of ansamycin antibiotics is described. Key steps for controlling the configuration of the three stereogenic centers involve a stereoselective Reformatsky-type reaction followed by a diastereoselective reduction of a beta-ketosulfoxide.
Obringer
Michel
M
Laboratoire de stereochimie associe au CNRS, UMR 7509, Universite de Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg Cedex 2, France.
Barbarotto
Marie
M
Choppin
Sabine
S
Colobert
Françoise
F
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D017828:Rifabutin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D011108:Polymers; C024617:polyol; D017828:Rifabutin