140226-71-7Relevant articles and documents
Total Syntheses of (-)-Englerins A/B, (+)-Orientalols E/F, and (-)-Oxyphyllol
Liu, Pengcai,Cui, Yutao,Chen, Kang,Zhou, Xinyue,Pan, Wenyan,Ren, Jun,Wang, Zhongwen
, p. 2517 - 2521 (2018)
(-)-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.