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An unprecedented ring expansion in the Macrolide series - synthesis of iso-bafilomycin A1

✍ Scribed by Stephen Hanessian; Qingchang Meng; Eric Olivier

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 284 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)73508-8

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✦ Synopsis

&&g& When treated with a reagent prepared from equimolar quantities of methyllithium and copper iodide, 7,21-d&O-TMS baf%mycin A2 3 undergoes ring expansion to give the 1 I-membered lactone homolog 5 in nearly quantitative yield. Acid hydrolysis gives iso-bafilomycin Al. Ring contraction to the original M-membered lactone takes place in the presence of fluoride ion. A mechanistic rationale and X-ray crystallographic evidence a~ PEsented. The hygrolide group of macrolide antibiotics comprises bafdomycin A1 1 and the hygrolidins23 whose structures are characterized by an unusual M-membered tetraenic lactone ring, containing a sugar-like appendage. The structure and absolute configuration of batilomycin Al 1 was established by X-ray crystallographic analysis4 and by NMR spectroscopy.~

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