Tetrahedron Letters p. 5393 - 5396 (1994)
Update date:2022-08-04
Topics:
Hanessian, Stephen
Meng, Quingchan
Olivier, Eric
When treated with a reagent prepared from equimolar quantities of methyllithium and copper iodide, 7,21-di-O-TMS bafilomycin A2 3 undergoes ring expansion to give the 18-membered lactone homolog 5 in nearly quantitative yield.Acid hydrolysis gives iso-bafilomycin A1.Ring contraction to the original 16-membered lactone takes place in the presence of fluoride ion.A mechanistic rationale and X-ray crystallographic evidence are presented.
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