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Published March 23, 2005 | Supplemental Material
Journal Article Open

Total Synthesis of Brasoside and Littoralisone


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.

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Supplemental Material - ja050064fsi20050105_083337.pdf


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