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Total Synthesis of Damirone C, Makaluvamine O, Makaluvone, Batzelline C and Batzelline D
Author(s) -
Backenköhler Jana,
Spindler Stefanie,
Spiteller Peter
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700285
Subject(s) - intramolecular force , total synthesis , halogenation , stereochemistry , quinoline , chemistry , biomimetic synthesis , organic chemistry
The first total synthesis of makaluvamine O and batzelline D, pyrroloquinoline alkaloids isolated from marine sponges, are described. Key steps in the biomimetic synthesis are an intramolecular Michael addition leading to the pyrrolo[4,3,2‐ de ]quinoline core and the following selective halogenation at C‐6 position with NBS/NCS. Moreover, the related marine alkaloids damirone C, makaluvone and batzelline C were synthesised via this approach.