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Radical cyclization of β-alkoxyacrylates: Stereoselective synthesis of (−)-trans-Kumausyne

✍ Scribed by Eun Lee; Sang-Ku Yoo; Young-Shin Cho; Hwan-Sung Cheon; You Hoon Chong

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
109 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

trans-Kumausyne was synthesized from D-(+)-xylose. Radical cycLization reaction of a I]-alkoxyacrylate intermediate proceeded stereoselectively to give a tetrahydrofuranyl product with correct stereochemistry.

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Radical cyclization reaction of a bis(~-alkoxyacrylate) intermediate prepared from (-)-diethyl D-tartrate proceeded stereoselectively to give a 2,6-dioxabicyclo[3.3.0]octane product, which was converted into a known intermediate in the synthesis of kumausallene.