Divergent Total Syntheses of Enmein‐Type Natural Products: (−)‐Enmein, (−)‐Isodocarpin, and (−)‐Sculponin R. Issue 21 (26th April 2018)

• Record Type: Journal Article
• Authors: Pan, Saiyong; Chen, Sicong; Dong, Guangbin
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 21(2018)
• Page Start: 6333
• Page End: 6336
• Publication Date: 2018-04-26
• Subjects: divergent synthesis -- enmein -- natural product synthesis -- terpenes -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201803709
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Divergent total syntheses of the enmein‐type natural products (−)‐enmein, (−)‐isodocarpin, and (−)‐sculponin R have been achieved in a concise fashion. Key features of the strategy include 1) an efficient early‐stage cage formation to control succeeding diastereoselectivity, 2) a one‐pot acylation/akylation/lactonization to construct the C‐ring and C8 quarternary center, 3) a reductive alkenylation approach to construct the enmain D/E rings and 4) a flexible route to allow divergent syntheses of three natural products. Abstract : Three bags full : Total syntheses of the enmein‐type natural products (−)‐enmein, (−)‐isodocarpin, and (−)‐sculponin R were achieved in a divergent and concise fashion. The common key intermediate contains a half‐cage structure.