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Total Synthesis of Premithramycinone H and Related Anthrapyran Antibiotics
Author(s) -
Krohn Karsten,
Vitz Jürgen
Publication year - 2004
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.200300451
Subject(s) - chemistry , natural product , derivative (finance) , total synthesis , cleavage (geology) , stereochemistry , antibiotics , molar ratio , pyran , organic chemistry , biochemistry , catalysis , geotechnical engineering , fracture (geology) , financial economics , engineering , economics
Two approaches are described for the preparation of 2‐(1′,3′‐dioxoalkyl)‐substituted 1‐hydroxyanthraquinones 10a − d and 20a − c , which were cyclized in a biomimetic‐type reaction to the anthra[1,2‐ b ]pyran skeletons 11a − d and 21a − c of the heydamycin‐ or pluramycin‐type antibiotics. Cleavage of the methyl ethers afforded the natural product premithramycinone H ( 2 ). The simple derivative 11b showed inhibition of the A431 cell line in µmolar concentrations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)