Lycopodium alkaloids, a unique family of biologically important natural products isolated and characterized from various species of Lycopodium(sensu lato), have attracted extensive attention from chemists and pharmaci...Lycopodium alkaloids, a unique family of biologically important natural products isolated and characterized from various species of Lycopodium(sensu lato), have attracted extensive attention from chemists and pharmacists in the past three decades. Michael addition-based cyclization has been successfully employed as an elegant and efficient ring-construction protocol of constructing key cyclohexanone intermediates in the total synthesis of Lycopodium alkaloids. This mini-review chooses and summarizes several representative total syntheses of various Lycopodium alkaloids in which intramolecular Michael addition severed as the key methodology.展开更多
Summary of main observation and conclusion A total synthesis of 6,7,9,10,12,12o-hexahydro-2-methyl-(2R/4αS,12α5)-2H,5H-benzo[e]pyrrolo-[3,2;l-ij]quinolone-4;ll(1H,3H)-dione(1),a unique pyrroloquinolone-type Lycopodi...Summary of main observation and conclusion A total synthesis of 6,7,9,10,12,12o-hexahydro-2-methyl-(2R/4αS,12α5)-2H,5H-benzo[e]pyrrolo-[3,2;l-ij]quinolone-4;ll(1H,3H)-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.展开更多
文摘Lycopodium alkaloids, a unique family of biologically important natural products isolated and characterized from various species of Lycopodium(sensu lato), have attracted extensive attention from chemists and pharmacists in the past three decades. Michael addition-based cyclization has been successfully employed as an elegant and efficient ring-construction protocol of constructing key cyclohexanone intermediates in the total synthesis of Lycopodium alkaloids. This mini-review chooses and summarizes several representative total syntheses of various Lycopodium alkaloids in which intramolecular Michael addition severed as the key methodology.
基金Financial support from the National Natural Science Foundation of China(Nos.21532002,21761142001 and 21778031)the National Key Research and Development Program(No.2018YFCO310900)is greatly appreciateq.
文摘Summary of main observation and conclusion A total synthesis of 6,7,9,10,12,12o-hexahydro-2-methyl-(2R/4αS,12α5)-2H,5H-benzo[e]pyrrolo-[3,2;l-ij]quinolone-4;ll(1H,3H)-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.
