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An Approach to the Synthesis of the Manzamine Alkaloids Via the Vinylogous Amide PH otocyclo A ddition/ R etro‐Mannich Fragmentation/ M annich Closure Cascade (pharM)
Author(s) -
Winkler Jeffrey D.,
Stelmach John E.,
Siegel Miles G.,
Haddad Nizar,
Axten Jeffrey,
Dailey William P.
Publication year - 1997
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.199700008
Subject(s) - chemistry , fragmentation (computing) , amide , stereochemistry , closure (psychology) , medicinal chemistry , organic chemistry , economics , market economy , computer science , operating system
The application of the vinylogous amide [2+2] photocycloaddition/retro‐Mannich fragmentation/ M annich 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.