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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 by Hiromichi Fujioka; Satoshi Matsuda; Mai Horai; Eri Fujii; Maiko Morishita; Natsuko Nishiguchi; Kayoko Hata; Yasuyuki Kita is a Chemistry article available to read on EtoBox.
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## Abstract 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(OCOCF~3~)~2~ in the presence of H~2~O 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.
Who reads 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?
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- Author
- Hiromichi Fujioka; Satoshi Matsuda; Mai Horai; Eri Fujii; Maiko Morishita; Natsuko Nishiguchi; Kayoko Hata; Yasuyuki Kita
- Publisher
- John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 0947-6539)
- Published
- 2007
- Language
- EN
- Field
- Chemistry (Physical Sciences)