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Total Synthesis of Mycenarubin A, Sanguinolentaquinone and Mycenaflavin B and their Cytotoxic Activities
Author(s) -
Backenköhler Jana,
Reck Bernhard,
Plaumann Markus,
Spiteller Peter
Publication year - 2018
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.201800417
Subject(s) - chemistry , total synthesis , stereochemistry , yield (engineering) , decarboxylation , alkylation , cytotoxic t cell , alkaloid , ring (chemistry) , in vitro , organic chemistry , biochemistry , catalysis , materials science , metallurgy
Here we report the first total synthesis of the fungal alkaloids mycenarubin A, sanguinolentaquinone and mycenaflavin B. The pyrroloquinoline alkaloid mycenarubin A was obtained in 10 steps (21 % total yield, 92 % ee ) from the known key precursor 6,7‐bis(benzyloxy)indole by an asymmetric alkylation and a biomimetic ring closure as the key steps. The indolo‐6,7‐quinone sanguinolentaquinone was obtained in eight steps (28 % total yield). Mycenaflavin B was also obtained in eight steps starting from the same key precursor (total yield 15 %) by a biomimetic ring closure and an acid‐catalysed decarboxylation reaction as the key steps. The cytotoxic activities of mycenarubin A and mycenaflavin B were evaluated against mouse fibroblasts (L929) and human malignant melanoma cells (RPMI‐7951).