A new access to ring-fused cyclopropanols through samarium diiodide-induced 3- exo-trig-cyclisations

Benzobicyclic δ-oxo-α,β-unsaturated esters easily prepared from tetralones or benzosuberone, readily cyclise in the presence of samarium diiodide and tert-butanol according to a totally syn mode, leading selectively to ‘cis’ ring-fused cyclopropanols that spontaneously lactonise to tetracyclic compo...

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Bibliographic Details
Published inTetrahedron letters Vol. 48; no. 46; pp. 8234 - 8237
Main Authors Zriba, Riadh, Bezzenine-Lafollée, Sophie, Guibé, François, Magnier-Bouvier, Caroline
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 12.11.2007
Elsevier
Subjects
Chemistry
Chemistry, Organic
Cyclisations
Cyclopropanols
Diastereoselectivity
Physical Sciences
Radicals
Samarium
Science & Technology
Cyclisations
Samarium
Cyclopropanols
Diastereoselectivity
Radicals
samarium
cyclisations
radicals
SMI2
IODIDE
CHEMISTRY
DELTA-OXO-ALPHA,BETA-UNSATURATED ESTERS
SMI2-MEDIATED 3-EXO-TRIG CYCLIZATION
cyclopropanols
diastereoselectivity
DERIVATIVES
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Summary:Benzobicyclic δ-oxo-α,β-unsaturated esters easily prepared from tetralones or benzosuberone, readily cyclise in the presence of samarium diiodide and tert-butanol according to a totally syn mode, leading selectively to ‘cis’ ring-fused cyclopropanols that spontaneously lactonise to tetracyclic compounds.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.09.071