Facile and efficient synthesis of lactols by a domino reaction of 2,3-epoxy alcohols with a hypervalent iodine(III) reagent and its application to the synthesis of lactones and the asymmetric synthesis of (+)-tanikolide

被引：37

作者：

Fujioka, Hiromichi ^{[1
]}

Matsuda, Satoshi ^{[1
]}

Horai, Mai ^{[1
]}

Fujii, Eri ^{[1
]}

Morishita, Maiko ^{[1
]}

Nishiguchi, Natsuko ^{[1
]}

Hata, Kayoko ^{[1
]}

Kita, Yasuyuki ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2007年 / 13卷 / 18期

关键词：

alcohols; domino reactions; iodine; lactols; lactones;

D O I：

10.1002/chem.200601341

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The domino reaction of 2,3-epoxy-1-alcohol derivatives, namely tetrasubstituted 2,3-epoxy-1-alcohols and 2- or 3-alkyl trisubstituted 2,3-epoxy- 1-alcohols, with PhI(OCOCF3)(2) in the presence of H2O is described in detail. In this reaction, several types of lactol derivatives can be directly obtained from the 2,3-epoxy-1-alcohol derivatives in a single operation. The obtained lactols were successively converted into the corresponding lactones. This reaction is applicable to the construction of optically active lactone compounds. The asymmetric total synthesis of (+)-tanikolide, an antifungal marine natural product, has been effectively achieved by using this reaction.

引用

页码：5238 / 5248

页数：11

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