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Front Cover: Synthesis and Absolute Stereochemical Reassignment of Mukanadin F: A Study of Isomerization of Bromopyrrole Alkaloids with Implications on Marine Natural Product Isolation (Eur. J. Org. Chem. 24/2018)
Author(s) -
van Rensburg Michelle,
Copp Brent R.,
Barker David
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800935
Subject(s) - isomerization , chemistry , front cover , natural product , enantiomer , sponge , stereochemistry , cover (algebra) , absolute configuration , total synthesis , organic chemistry , catalysis , botany , mechanical engineering , engineering , biology
The Front Cover shows mukanadin F, a bromopyrrole marine natural product isolated from an Okinawan sponge belonging to the Agelas species. Synthesis of mukanadin F unexpectedly showed that both enantiomers undergo isomerisation. Further isomerisation and racemisation studies concluded that these types of alkaloids readily undergo configuration transformation under benign conditions, such as sunlight and methanol. These findings helped in the reassignment of the absolute stereochemistry of isolated mukanadin F. Pictured is an Indonesian specimen of Agelas nakamurai sponge taken by Dr Merrick Ekins, Queensland Museum. More information can be found in the Full Paper by D. Barker et al.