Volume 31, Issue 5
Heterocyclic Compounds
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ChemInform Abstract: Efficient Route to Functionalized Eight-Membered Lactones Based on Intramolecular Silicon-Directed Acylative Ring-Opening Reactions of 3-(Tetrahydro-2-furyl)propanoic Acid Derivatives.

Hidenori Ohi

Hidenori Ohi

Fac. Pharm. Sci., Nagasaki Univ., Bunkyo, Nagasaki 852, Japan

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Susumu Inoue

Susumu Inoue

Fac. Pharm. Sci., Nagasaki Univ., Bunkyo, Nagasaki 852, Japan

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Yoshiharu Iwabuchi

Yoshiharu Iwabuchi

Fac. Pharm. Sci., Nagasaki Univ., Bunkyo, Nagasaki 852, Japan

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Hiroshi Irie

Hiroshi Irie

Fac. Pharm. Sci., Nagasaki Univ., Bunkyo, Nagasaki 852, Japan

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Susumi Hatakeyama

Susumi Hatakeyama

Fac. Pharm. Sci., Nagasaki Univ., Bunkyo, Nagasaki 852, Japan

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First published: 11 June 2010

Abstract

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ChemInform Abstract

The ring enlargement of furylpropanoic acids (I), (IV), and (VI) by treatment with trifluoroacetic anhydride is an effective method for the synthesis of eight-membered lactones. In some cases, products of other ring-rearrangements are isolated additionally in low yields [from compound (Id) and (IVc)] or exclusively [from compounds (III)].

chemical structure image

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