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Chemistry. 2000 Nov 3;6(21):3887-96.
Biomimetic synthesis of the racemic angucyclinones of the aquayamycin and WP 3688-2 types.
Krohn K, Frese P, Florke U.
Fachbereich Chemie und Chemietechnik der Universitat Paderborn, Germany. khemie.uni-paderborn.de
The first synthesis of the racemic 8-deoxy WP3688-2 angucycline antibiotic (3), with characteristic cis-hydroxy groups at C-4 a and C-12b, is reported. Key steps involve the coupling, mediated by samarium diiodide, of the bicyclic trione 37 to the tricyclic cis-diol 39. Biomimetic aldol cyclization of the corresponding dione 41 gave a mixture of the tetracyclic cis- and trans-3,4a-diols 42 and 43, which were oxidized by cerium ammonium nitrate to the quinones 45 and 3. The synthetic compounds 45 and 3 corresponded in configuration to the angucycline antibiotics aquayamicin (1) and WP 3688-2 (2), respectively.
online pharmacy ref. source: www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11126949&dopt=Abstract
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