Published March 23, 2005
| Supplemental Material
Journal Article
Open
Total Synthesis of Brasoside and Littoralisone
- Creators
- Mangion, Ian K.
- MacMillan, David W. C.
Abstract
The first total syntheses of littoralisone (1) and brasoside (2) have been achieved in 13 overall steps. Both natural products are forged from a common intermediate which is rapidly assembled using organocatalytic technology, including a proline-catalyzed α-aminoxylation and a contra-thermodynamic intramolecular Michael addition. Application of the two-step carbohydrate synthesis technology has enabled to access a selectively substituted glucose derivative for use as an intramolecular cycloaddition tether. This synthesis culminates with an intramolecular [2+2] photocycloaddition that serves to support the proposed biosynthetic origins of 1 from 2.
Additional Information
© 2005 American Chemical Society. Received 5 January 2005. Published online 26 February 2005. Published in print 1 March 2005. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from Amgen and Merck. I.K.M. is grateful for a NSF predoctoral fellowship. Amanda Reider is thanked for experimental contributions.Attached Files
Supplemental Material - ja050064fsi20050105_083337.pdf
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ja050064fsi20050105_083337.pdf
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Additional details
- Eprint ID
- 76790
- DOI
- 10.1021/ja050064f
- Resolver ID
- CaltechAUTHORS:20170421-071046814
- R01 GM66142-01
- NIH
- Amgen
- Merck
- NSF Predoctoral Fellowship
- Created
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2017-04-21Created from EPrint's datestamp field
- Updated
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2021-11-15Created from EPrint's last_modified field