Total synthesis of (+/-)-mycothiazole and formal enantioselective approach.
[Reaction: see text] A total synthesis of (+/-)-mycothiazole and a formal enantioselective approach have been achieved from 2,4-dibromothiazole. A chain extension of a homoallylic alcohol proceeding through an unsaturated sultone intermediate, generated by ring-closing metathesis, was used as a key step for the elaboration of the conjugated (Z)-dienol moiety.
Le Flohic
Alexandre
A
Laboratoire de Chimie Organique, associé au CNRS, ESPCI, 10 rue Vauquelin, 75231 Paris 05, France.
Meyer
Christophe
C
Cossy
Janine
J
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry*
D000970:Antineoplastic Agents; D013844:Thiazoles; C508681:mycothiazole