✦ LIBER ✦

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

✍ Scribed by Hiromichi Fujioka; Satoshi Matsuda; Mai Horai; Eri Fujii; Maiko Morishita; Natsuko Nishiguchi; Kayoko Hata; Yasuyuki Kita

Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 274 KB
Volume: 13
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200601341

No coin nor oath required. For personal study only.

✦ Synopsis

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.

📜 SIMILAR VOLUMES

The Efficient Synthesis of Morphinandien

The Efficient Synthesis of Morphinandienone Alkaloids by Using a Combination of Hypervalent Iodine(III) Reagent and Heteropoly Acid

✍ Hiromi Hamamoto; Yukiko Shiozaki; Hisanori Nambu; Kayoko Hata; Hirofumi Tohma; Y 📂 Article 📅 2004 🏛 John Wiley and Sons 🌐 English ⚖ 196 KB 👁 1 views

The Efficient Direct Synthesis of N,O-Ac

The Efficient Direct Synthesis of N,O-Acetal Compounds as Key Intermediates of Discorhabdin A: Oxidative Fragmentation Reaction of α-Amino Acids or β-Amino Alcohols by Using Hypervalent Iodine(III) Reagents

✍ Yu Harayama; Masako Yoshida; Daigo Kamimura; Yasufumi Wada; Yasuyuki Kita 📂 Article 📅 2006 🏛 John Wiley and Sons 🌐 English ⚖ 158 KB 👁 1 views

New Highly Asymmetric Henry Reaction Cat

New Highly Asymmetric Henry Reaction Catalyzed by CuII and a C1-Symmetric Aminopyridine Ligand, and Its Application to the Synthesis of Miconazole

✍ Gonzalo Blay; Luis R. Domingo; Victor Hernández-Olmos; José R. Pedro 📂 Article 📅 2008 🏛 John Wiley and Sons 🌐 English ⚖ 290 KB 👁 1 views

ChemInform Abstract: Hypervalent Iodine

ChemInform Abstract: Hypervalent Iodine in Synthesis. Part 24. A Facile Method for the Preparation of Arylsulfinic Esters: Oxidation of Disulfides or Thiophenols by Phenyliodine(III) Bis(trifluoroacetate) in the Presence of Alcohols.

✍ M. XIA; Z.-C. CHEN 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB

Hypervalent Iodine in Synthesis. Part 24. A Facile Method for the Preparation of Arylsulfinic Esters: Oxidation of Disulfides or Thiophenols by Phenyliodine(III) Bis(trifluoroacetate) in the Presence of Alcohols. -The oxidative reaction of disulfides (I) and thiophenols (IV) occurs readily in a sin

ChemInform Abstract: Hypervalent Iodine

ChemInform Abstract: Hypervalent Iodine in Synthesis. Part 21. A Facile Method for the Preparation of Thiosulfonic S-Esters by the Oxidation of Diaryl Disulfides or Thiophenols with Phenyliodine(III) Bis(trifluoroacetate).

✍ M. XIA; Z.-C. CHEN 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 34 KB