Stereocontrolled total synthesis of (±)-lubiminol, a spirovetivane phytoalexin
✍ Scribed by Chuzo Iwata; Hitoshi Kubota; Minoru Yamada; Yoshiji Takemoto; Shuji Uchida; Tetsuaki Tanaka; Takeshi Imanishi
- Book ID
- 104233746
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 231 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A total synthesis of (+)-lubiminol, one of the spirovetivane phytoalexins, was accomplished under a high stereocontrol of all five asymmetric carbon centers.
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Rearrangement of Cyclobutyl Carbinyl Radicals: Total Synthesis of the Spirovetivane Phytoalexin (±)-Lubiminol. -The total synthesis of title compound (VI) relies on the intramolecular photolytic (2 + 2) cycloaddition of the key intermediate (I). The stereoselectively resulting photoadduct (II) is t
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Recent synthetic and degradative studies (1) have necessitated a structural revision of the entire class of vetivane sesquiterpenes whereby the previously accepted bicycIoC5.3.01decane carbon framework (I) must be discarded in favor of the spiroC4. Sldecane system (II).