1. Total Syntheses of (-)-Englerins A/B, (+)-Orientalols E/F, and (-)-Oxyphyllol.
- Author
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Pengcai Liu, Yutao Cui, Kang Chen, Xinyue Zhou, Wenyan Pan, Jun Ren, and Zhongwen Wang
- Subjects
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SESQUITERPENES , *STEREOSELECTIVE reactions , *CYCLOPROPANE , *HYDROXYL group , *CHEMICAL precursors - Abstract
(-)-Englerin A was synthesized in 20 steps from the commercially available material (R)-(+)-limonene. In addition, (-)-englerin B, (+)-orientalol E/F and (-)-oxyphyllol were obtained from the intermediate in the route. The key steps include a hydroxyl-directing stereoselective and regioselective intramolecular cyclopropanation and a multi-gram-scale stereoselective formal intramolecular [3 + 2] cross cycloaddition ([3 + 2]-IMCC) of a cyclopropane 1,1-diester with a carbonyl. A precursor of 7,10-diastereoisomer of englerins was also obtained. [ABSTRACT FROM AUTHOR]
- Published
- 2018
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