Isolation, Enantioselective Total Synthesis and Structure Determination of the Anthrapyran Metabolite SS 43405‐e | Zendy

Tietze Lutz F. | Zendy; Singidi Ramakrishna Reddy | Zendy; Gericke Kersten M. | Zendy; Böckemeier Henning | Zendy; Laatsch Hartmut | Zendy

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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)

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