Israel Journal of Chemistry p. 47 - 67 (1997)
Update date:2022-08-02
Topics: Synthesis Photocycloaddition Cascade Manzamine alkaloids Vinylogous amide Retro-Mannich fragmentation Mannich closure PhaRM
Winkler, Jeffrey D.
Stelmach, John E.
Siegel, Miles G.
Haddad, Nizar
Axten, Jeffrey
Dailey III, William P.
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 pharM closure product to generate the pentacyclic ring system.
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