Highly Efficient Total Synthesis of (+)-Citreoviral

• Published in: Angewandte Chemie (International ed.) Vol. 43; no. 24; pp. 3175 - 3177
• Main Authors: Murata, Yoshihisa, Kamino, Tomoyuki, Aoki, Toshiaki, Hosokawa, Seijiro, Kobayashi, Susumu
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 14.06.2004; WILEY‐VCH Verlag; Wiley
• Subjects: alcohols; Alcohols - chemistry; aldol reaction; Bridged Bicyclo Compounds - chemical synthesis; Bridged Bicyclo Compounds - chemistry; Chemistry; Chemistry, Multidisciplinary; Enzyme Inhibitors - chemical synthesis; Furans - chemical synthesis; Furans - chemistry; Indicators and Reagents; lactones; Molecular Conformation; natural products; Physical Sciences; Science & Technology; Stereoisomerism; total synthesis; FORMAL SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; HYDROXYLATION; alcohols; Aldol reaction; CITREOVIRIDIN; natural products; lactones; (-)-CITREOVIRIDIN; (+/-)-CITREOVIRIDIN; total synthesis; SUBSTITUTED TETRAHYDROFURANS; DERIVATIVES; BINDING
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.200454212

Only eight steps were required for the total synthesis of (+)‐citreoviral (3) from chiral imide 1 in 18 % overall yield. The key steps included a highly anti‐selective aldol reaction, the stereoselective iodolactonization of a γ,δ‐unsaturated β‐hydroxyimide, and an intramolecular SN2 reaction of a tertiary alcohol to form intermediate 2.