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Total Syntheses of (-)-Englerins A/B, (+)-Orientalols E/F, and (-)-Oxyphyllol

Total Syntheses of (-)-Englerins A/B, (+)-Orientalols E/F, and (-)-Oxyphyllol

Pengcai Liu, Yutao Cui, Kang Chen, Xinyue Zhou, Wenyan Pan, Jun Ren, Zhongwen Wang

Org Lett. 2018 May 4;20(9):2517-2521.

PMID: 29664306

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1094250131	(-)-Englerin B		1094250-13-1	Price

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