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A Practical Synthesis of (±)-α-Isosparteine from a Tetraoxobispidine Core†
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Section:Abstract
The title alkaloid was synthesized in racemic form from 3,7-diallyl-2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (7) by a regioselective diallylation reaction followed by double ring-closing olefin metathesis and exhaustive reduction. Tetraoxobispidine 7 was itself prepared in three simple operations from dimethyl malonate. The entire sequence to α-isosparteine was conducted on a multigram scale and proceeded without recourse to chromatography.
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
A Flexible Route to Chiral 2-endo-Substituted 9-Oxabispidines and Their Application in the Enantioselective Oxidation of Secondary Alcohols
Matthias Breuning, Melanie Steiner, Christian Mehler, Alexander Paasche and David HeinThe Journal of Organic Chemistry2009 74 (3), 1407-1410A Flexible Route to Chiral 2-endo-Substituted 9-Oxabispidines and Their Application in the Enantioselective Oxidation of Secondary Alcohols
Matthias Breuning, Melanie Steiner, Christian Mehler, Alexander Paasche and David HeinThe Journal of Organic Chemistry2009 74 (3), 1407-1410A new and flexible route to enantiomerically pure bi- and tricyclic 9-oxabispidines has been developed with use of (1R,5S)-7-methyl-2-oxo-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester as the common late-stage intermediate. The 9-...
Structural Features and Reactivity of (Sparteine)PdCl2: A Model for Selectivity in the Oxidative Kinetic Resolution of Secondary Alcohols
Raissa M. Trend and Brian M. StoltzJournal of the American Chemical Society2008 130 (47), 15957-15966Structural Features and Reactivity of (Sparteine)PdCl2: A Model for Selectivity in the Oxidative Kinetic Resolution of Secondary Alcohols
Raissa M. Trend and Brian M. StoltzJournal of the American Chemical Society2008 130 (47), 15957-15966The chiral ligand (−)-sparteine and PdCl2 catalyze the enantioselective oxidation of secondary alcohols to ketones and thus effect a kinetic resolution. The structural features of sparteine that led to the selectivity observed in the reaction were not ...
Total Synthesis of (±)-α-Isosparteine, (±)-β-Isosparteine, and (±)-Sparteine from a Common Tetraoxobispidine Intermediate
Neil R. Norcross, John P. Melbardis, Margarita Ferris Solera, Mark A. Sephton, Colin Kilner, Lev N. Zakharov, Peter C. Astles, Stuart L. Warriner and Paul R. BlakemoreThe Journal of Organic Chemistry2008 73 (20), 7939-7951Total Synthesis of (±)-α-Isosparteine, (±)-β-Isosparteine, and (±)-Sparteine from a Common Tetraoxobispidine Intermediate
Neil R. Norcross, John P. Melbardis, Margarita Ferris Solera, Mark A. Sephton, Colin Kilner, Lev N. Zakharov, Peter C. Astles, Stuart L. Warriner and Paul R. BlakemoreThe Journal of Organic Chemistry2008 73 (20), 7939-7951The three title alkaloids were separately prepared in stereocontrolled fashion from a common tetraoxobispidine precursor, 3,7-diallyl-2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (16). Bisimide 16 was generated from malonate via acid promoted ...
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History
- Published In Issue October 13, 2005
- Received August 9, 2005
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