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Studies towards the Leucetta ‐Derived Alkaloids Spirocalcaridine A and B – Possible Biosynthetic Implications
Author(s) -
Koswatta Panduka B.,
Das Jayanta,
Yousufuddin Muhammed,
Lovely Carl J.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403650
Subject(s) - chemistry , methylamine , formamide , electrophile , formamides , stereochemistry , aryl , catalysis , organic chemistry , alkyl
An exploration of an abiotic approach to spirocalcaridines A and B is described centered on electrophile‐induced dearomatizing spirocyclization of aryl enyne derivatives. Elaboration of the α‐iodoenone through an Ullmann‐like, copper‐catalyzed amidation provided a formamide, which upon treatment with methylamine undergoes a dienol‐arene rearrangement to provide the corresponding kealiinine‐like framework. This observation suggests a possible biosynthetic links between the spirocalcaridine and naphthimidazole group of Leucetta alkaloids.