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An Eight‐Step Total Synthesis of Pyrroloquinolone‐Type Lycopodium Alkaloid via a Tandem Annulation Approach †
Author(s) -
Zhong LinRui,
Yang Yuanjie,
Huang BingBing,
Yao ZhuJun
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000273
Subject(s) - chemistry , total synthesis , annulation , tandem , stereocenter , stereochemistry , alkaloid , yield (engineering) , organic chemistry , enantioselective synthesis , materials science , composite material , catalysis , metallurgy
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.