Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 29, Pages 8805-8821Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000804
Keywords
angucyclinone; catalysis; cobalt; cycloaddition; natural products
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Funding
- Landesgraduiertenforderung Baden-Wurttemberg
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A cobalt(I)-mediated convergent and asymmetric total synthesis of angucyclinones with an aromatic B ring has been developed. In the course of our research, we synthesized three naturally occurring anguclinone derivatives, namely, (+)-rubiginone B-2 (1), (-)-8-O-methyltetrangomycin (2), and (-)-tetrangomycin (3). By combining 3-hydroxybenzoic acid, 3-methoxybenzoic acid, citronellal, and geraniol as starting materials in a convergent way, we were able to synthesize chiral triyne chains, which were cyclized with [CpCo(C2H4)(2)] (CP = cyclopentadienyl) by means of an intramolecular [2+2+2] cycloaddition to their corresponding tetrahydrobenzo[a]anthracenes. Successive oxidation and deprotection steps led to the above-mentioned natural products 1-3.
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