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Studies on the Synthesis of Durhamycin A: Stereoselective Synthesis of a Model Aglycone
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Section:Abstract
A stereoselective synthesis of the model aglycone corresponding to the anti-HIV aureolic acids durhamycins A (1) and B (2) is described.
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
Mild and Expedient Asymmetric Reductions of α,β-Unsaturated Alkenyl and Alkynyl Ketones by TarB-NO2 and Mechanistic Investigations of Ketone Reduction
Scott Eagon, Cassandra DeLieto, William J. McDonald, Dustin Haddenham, Jaime Saavedra, Jinsoo Kim, and Bakthan SingaramThe Journal of Organic Chemistry2010 75 (22), 7717-7725Mild and Expedient Asymmetric Reductions of α,β-Unsaturated Alkenyl and Alkynyl Ketones by TarB-NO2 and Mechanistic Investigations of Ketone Reduction
Scott Eagon, Cassandra DeLieto, William J. McDonald, Dustin Haddenham, Jaime Saavedra, Jinsoo Kim, and Bakthan SingaramThe Journal of Organic Chemistry2010 75 (22), 7717-7725A facile and mild reduction procedure is reported for the preparation of chiral allylic and propargyl alcohols in high enantiomeric purity. Under optimized conditions, alkynyl and alkenyl ketones were reduced by TarB-NO2 and NaBH4 at 25 °C in 1 h to ...
Stereoselective Synthesis of γ-Substituted (Z)-Allylic Boranes via Kinetically Controlled Hydroboration of Allenes with 10-TMS-9-borabicyclo[3.3.2]decane
Jeremy Kister, Amy C. DeBaillie, Ricardo Lira and William R. RoushJournal of the American Chemical Society2009 131 (40), 14174-14175Stereoselective Synthesis of γ-Substituted (Z)-Allylic Boranes via Kinetically Controlled Hydroboration of Allenes with 10-TMS-9-borabicyclo[3.3.2]decane
Jeremy Kister, Amy C. DeBaillie, Ricardo Lira and William R. RoushJournal of the American Chemical Society2009 131 (40), 14174-14175Kinetically controlled hydroboration of allenes 8 and 14a−d with the readily accessible Soderquist borane 7, which is generated in situ from borohydride 6, constitutes a convenient and preparatively useful method for synthesis of (Z)-γ-(substituted)...
Highly Enantioselective and Regioselective Carbonyl Reduction of Cyclic α,β-Unsaturated Ketones Using TarB-NO2 and Sodium Borohydride
Jinsoo Kim, John Bruning, Kevin E. Park, David J. Lee and Bakthan SingaramOrganic Letters2009 11 (19), 4358-4361Highly Enantioselective and Regioselective Carbonyl Reduction of Cyclic α,β-Unsaturated Ketones Using TarB-NO2 and Sodium Borohydride
Jinsoo Kim, John Bruning, Kevin E. Park, David J. Lee and Bakthan SingaramOrganic Letters2009 11 (19), 4358-4361Asymmetric 1,2-reduction of α,β-unsaturated ketones using TarB-NO2 and NaBH4 is reported. Simple cycloalkenones give products in low enantiomeric excess. However, cycloalkenones with α-substituents, such as halides, alkyl, and aryl, have been ...
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History
- Published In Issue October 16, 2008
- Article ASAPSeptember 23, 2008
- Received: August 12, 2008
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