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Isolation, Enantioselective Total Synthesis and Structure Determination of the Anthrapyran Metabolite SS 43405‐e
Author(s) -
Tietze Lutz F.,
Singidi Ramakrishna Reddy,
Gericke Kersten M.,
Böckemeier Henning,
Laatsch Hartmut
Publication year - 2007
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.200700534
Subject(s) - enantioselective synthesis , chemistry , total synthesis , enantiopure drug , metabolite , aldehyde , ketone , absolute configuration , derivative (finance) , stereochemistry , anthraquinone , natural product , secondary metabolite , organic chemistry , combinatorial chemistry , catalysis , biochemistry , financial economics , economics , gene
The first enantioselective total synthesis of the anthrapyran metabolite SS 43405‐e, isolated from a marine‐derived streptomycete, is described, which also allows the determination of the so far unknown absolute ( R ) configuration of the natural product. For the synthesis the bromoanthracene derivative 3 is lithiated and coupled with the enantiopure aldehyde ( S )‐ 4 to give 9 , which is oxidatively transformed into the corresponding anthraquinone 10 and further into the ketone 2 . The final step is the cyclization of 2 under acidic conditions to give the desired antibiotic ( S )‐ 1 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)