TY - JOUR
T1 - Tandem 1,3-dipolar cycloaddition and electrophilic cyclization reactions
T2 - Cyclic ether subunits of polyether antibiotics from unsaturated isoxazolines
AU - Kurth, Mark J.
AU - Rodriguez, Michael J.
AU - Olmstead, Marilyn M.
PY - 1990
Y1 - 1990
N2 - A new strategy for the construction of polyether antibiotic substructural units [spiroketals (I), tetrahydrofurans (II), and tetrahydropyrans (III)] consisting of bis-addition of an oxygen nucleophile across an α,ω-diene moiety (i.e., IV) is described. The method exploits a tandem 1,3-dipolar cycloaddition/electrophilic cyclization sequence that proceeds via the intermediacy of an isoxazoline. Experiments presented illustrate the versatility of this strategy, which provides a unique exploit of the control elements operative in dipolar cycloaddition and electrophilic cyclization chemistry.
AB - A new strategy for the construction of polyether antibiotic substructural units [spiroketals (I), tetrahydrofurans (II), and tetrahydropyrans (III)] consisting of bis-addition of an oxygen nucleophile across an α,ω-diene moiety (i.e., IV) is described. The method exploits a tandem 1,3-dipolar cycloaddition/electrophilic cyclization sequence that proceeds via the intermediacy of an isoxazoline. Experiments presented illustrate the versatility of this strategy, which provides a unique exploit of the control elements operative in dipolar cycloaddition and electrophilic cyclization chemistry.
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M3 - Article
AN - SCOPUS:0025232397
VL - 55
SP - 283
EP - 288
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 1
ER -