Published June 21, 2006
| Version Supplemental Material
Journal Article
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The Catalytic Enantioselective, Protecting Group-Free Total Synthesis of (+)-Dichroanone
Abstract
Herein we report the first enantioselective total synthesis of (+)-dichroanone, confirming the absolute configuration of the natural product. This protecting group-free route features the first application of our enantioselective Tsuji allylation in the context of a natural product total synthesis. Additionally, this 11-step preparation of the molecule from commercial material features a novel Kumada-aromatization strategy and a rapid sequence for the conversion of a phenol to a hydroxy-p-benzoquinone.
Additional Information
© 2006 American Chemical Society. Received 17 March 2006. Published online 26 May 2006. Published in print 1 June 2006. We are grateful to Eli Lilly (graduate fellowship to R.M.M.), Johnson & Johnson, Bristol-Myers Squibb, Merck, Amgen, and the Dreyfus Foundation for generous funding. Doug Behenna, J. T. Mohr, and Dr. Andrew Harned are acknowledged for helpful discussions.Attached Files
Supplemental Material - ja061853fsi20060511_015558.pdf
Supplemental Material - ja061853fsi20060511_015613.cif
Files
ja061853fsi20060511_015558.pdf
Additional details
Identifiers
- Eprint ID
- 74448
- DOI
- 10.1021/ja061853f
- Resolver ID
- CaltechAUTHORS:20170222-075015251
Related works
- Describes
- http://pubs.acs.org/doi/suppl/10.1021/ja061853f (URL)
Funding
- Johnson and Johnson
- Bristol-Myers Squibb
- Merck
- Amgen
- Camille and Henry Dreyfus Foundation
Dates
- Created
-
2017-02-22Created from EPrint's datestamp field
- Updated
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2021-11-11Created from EPrint's last_modified field