180211-03-4

Upstream product

• 50545-40-9 6,7-Bis(benzyloxy)indole 
• 30354-18-8 N,N-dimethyl(methylene)ammonium chloride 
• 33797-51-2 eschenmoser's salt 

Downstream Products

• 180211-07-8 6,7-Bis-benzyloxy-3-(2,2-dimethoxy-ethyl)-indole-1-carboxylic acid tert-butyl ester 
• 180211-05-6 6,7-Bis-benzyloxy-3-cyanomethyl-indole-1-carboxylic acid tert-butyl ester 
• 180211-06-7 6,7-Bis-benzyloxy-3-(2-oxo-ethyl)-indole-1-carboxylic acid tert-butyl ester 
• 180211-04-5 (6,7-Bis-benzyloxy-1H-indol-3-yl)-acetonitrile 

Relevant academic research and scientific papers

Total Synthesis of Mycenarubin A, Sanguinolentaquinone and Mycenaflavin B and their Cytotoxic Activities

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).

Pigments of fungi, 65: Synthesis of haematopodin - A pigment from the mushroom Mycena haematopus (Basidiomycetes)

Haematopodin (1), a pigment from fruit bodies of the mushroom Mycena haematopus, was synthesized from 6,7-bis-(benzyloxy)indole (5). Key steps in the synthesis were the addition of 3-[(2,4-dimethoxybenzyl)amino]-1-propanol (11) to the indolo-6,7-quinone 10 and cyclization of the resulting adduct 12 with trifluoroacetic acid. VCH Verlagsgesellschaft mbH, 1996.