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Total Synthesis of Brasoside and Littoralisone

Mangion, Ian K. and MacMillan, David W. C. (2005) Total Synthesis of Brasoside and Littoralisone. Journal of the American Chemical Society, 127 (11). pp. 3696-3697. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170421-071046814

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja050064fDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja050064fPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja050064fPublisherSupporting Information
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.
Funders:
Funding AgencyGrant Number
NIHR01 GM66142-01
AmgenUNSPECIFIED
MerckUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
Issue or Number:11
Record Number:CaltechAUTHORS:20170421-071046814
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170421-071046814
Official Citation:Total Synthesis of Brasoside and Littoralisone Ian K. Mangion and David W. C. MacMillan Journal of the American Chemical Society 2005 127 (11), 3696-3697 DOI: 10.1021/ja050064f
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76790
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:21 Apr 2017 18:13
Last Modified:03 Oct 2019 17:50

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