An Eight‐Step Total Synthesis of Pyrroloquinolone‐Type Lycopodium Alkaloid via a Tandem Annulation Approach†. Issue 12 (24th September 2020)

• Record Type: Journal Article
• Authors: Zhong, Lin‐Rui; Yang, Yuanjie; Huang, Bing‐Bing; Yao, Zhu‐Jun
• Is Part Of: Chinese journal of chemistry. Volume 38:Issue 12(2020)
• Page Start: 1560
• Page End: 1564
• Publication Date: 2020-09-24
• Subjects: K Lycopodium alkaloid -- Total synthesis -- Tandem annulation -- Pyrroloquinolone -- Imine‐enamine interchange; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202000273
• Languages: English
• ISSNs: 1001-604X

Abstract

Summary of main observation and conclusion: A total synthesis of 6, 7, 9, 10, 12, 12 a ‐hexahydro‐2‐methyl‐(2 R, 4 aS, 12 aS )‐2 H, 5 H ‐benzo[ e ]pyrrolo[3, 2, 1‐ ij ]quinolone‐4, 11(1 H, 3 H )‐dione (1 ), a unique pyrroloquinolone‐type Lycopodium alkaloid containing a complex 6/6/6/5 tetracyclic core, has been disclosed in eight steps and 38% overall yield. The reported synthesis features a short, efficient synthesis of the crucial multi‐substituted cyclohexanone intermediate with three stereogenic centers, and one‐pot generation of the complex 6/6/6/5 tetracyclic core in a single tandem step. Abstract : A total synthesis of (2 R, 4 aS, 12 aS )‐6, 7, 9, 10, 12, 12 a ‐hexahydro‐2‐methyl‐(5 H ‐benzo[ e ]pyrrolo[3, 2, 1‐ij]quinolone‐4, 11(1 H, 3 H )‐dione (1 ), a unique pyrroloquinolone‐type Lycopodium alkaloid containing a complex 6/6/6/5 tetracyclic core, has been accomplished in 8 steps and 38% overall yield. The reported synthesis features a short efficient preparation of the crucial multi‐substituted cyclohexanone intermediate with three stereochemical centers, and one‐pot generation of the complex 6/6/6/5 tetracyclic core in a single tandem step.