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Org Lett ; 18(12): 2868-71, 2016 06 17.
Article in English | MEDLINE | ID: mdl-27267744

ABSTRACT

Desmethyl erythronolides have emerged as macrolide targets that may prove effective against resistant bacteria. A five-step sequence to 4,10-didesmethyl (9S)-dihydroerythronolide A (1) from known cyclic bis[allene] 13 is reported. Key structural and mechanistic aspects of the synthesis are discussed along with catalytic allene osmylation. An improved route to 13 is also described.


Subject(s)
Alkadienes/chemistry , Anti-Bacterial Agents/chemical synthesis , Erythromycin/analogs & derivatives , Catalysis , Erythromycin/chemical synthesis , Molecular Structure , Stereoisomerism
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