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Synfacts 2011(2): 0121-0121
DOI: 10.1055/s-0030-1259215
DOI: 10.1055/s-0030-1259215
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New YorkTotal Synthesis of (+)-Roxaticin
Rezensent(en):Steven V. Ley, Catherine F. CarterS. B. Han, A. Hassan, I. S. Ku, M. J. Krische*
University of Texas at Austin, USA
Total Synthesis of (+)-Roxaticin via C-C Bond Forming Transfer Hydrogenation: A Departure from Stoichiometric Chiral Reagents, Auxiliaries and Premetalated Nucleophiles in Polyketide Construction
J. Am. Chem. Soc. 2010, 132: 15559-15561
University of Texas at Austin, USA
Total Synthesis of (+)-Roxaticin via C-C Bond Forming Transfer Hydrogenation: A Departure from Stoichiometric Chiral Reagents, Auxiliaries and Premetalated Nucleophiles in Polyketide Construction
J. Am. Chem. Soc. 2010, 132: 15559-15561
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
19. Januar 2011 (online)
Key words
(+)-roxaticin - cross-metathesis - C-C bond forming transfer hydrogenation
Significance
The oxo-polyene macrolide (+)-roxaticin has been a popular target for the synthetic community. This synthesis requires only 20 steps and is particularly efficient due to a lack of chiral auxiliary controlled reactions and redox manipulations.
Comment
The key step in the synthesis is a C-C bond forming transfer hydrogenation (e.g. A → C), which is used to form seven C-C bonds.