Efficient Synthesis of Dihydrofurans with Sulfide Groups by Ceric(IV) Ammonium Nitrate-Mediated Oxidative Cycloaddition of 1,3-Dicarbonyl Compounds to Vinyl Sulfides. Application to the Synthesis of Benzo[b]naphtho[2,3-d]furan-6,11-dione and First Total Synthesis of Millettocalyxins C and Pongamol Methyl Ether.
✍ Scribed by Yong Rok Lee; Keon Yong Kang; Gun Joon Lee; Won Kyong Lee
- Publisher
- John Wiley and Sons
- Year
- 2004
- Weight
- 162 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
2004 Furan derivatives Furan derivatives R 0060 Efficient Synthesis of Dihydrofurans with Sulfide Groups by Ceric(IV) Ammonium Nitrate-Mediated Oxidative Cycloaddition of 1,3-Dicarbonyl Compounds to Vinyl Sulfides. Application to the Synthesis of Benzo[b]naphtho[2,3-d]furan-6,11-dione and First Total Synthesis of Millettocalyxins C and Pongamol Methyl Ether. -A variety of 1,3-dicarbonyl compounds and vinyl sulfides undergo an oxidative CAN-mediated cycloaddition to give substituted dihydrofurans in moderate yields. The product (IIIc) is demonstrated to be a valuable starting material for the total synthesis of millettocalyxins C (XVa) and pongamol methyl ether (XVb). -(LEE*, Y.