An Approach to the Synthesis of the Manzamine Alkaloids Via the Vinylogous Amide PHotocycloAddition/Retro‐Mannich Fragmentation/Mannich Closure Cascade (pharM)

Autor: Winkler, Jeffrey D., Stelmach, John E., Siegel, Miles G., Haddad, Nizar, Axten, Jeffrey, Dailey, William P.
Zdroj: Israel Journal of Chemistry; 1997, Vol. 37 Issue: 1 p47-67, 21p
Abstrakt: The application of the vinylogous amide [2+2] photocycloaddition/retro‐Mannich fragmentation/Mannich closure cascade (pharM) to the synthesis of the pentacyclic ring system of the anti‐leukemic marine alkaloid manzamine A is presented. Two approaches to the synthesis of the requisite pentacycle are described: (a) the transannular photocycloaddition of an 18‐membered vinylogous amide; and (b) photocycloaddition of an acyclic vinylogous amide, followed by macrolactamization of the derived pharMclosure product to generate the pentacyclic ring system.
Databáze: Supplemental Index