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The Catalytic Enantioselective, Protecting Group-Free Total Synthesis of (+)-Dichroanone

McFadden, Ryan M. and Stoltz, Brian M. (2006) The Catalytic Enantioselective, Protecting Group-Free Total Synthesis of (+)-Dichroanone. Journal of the American Chemical Society, 128 (24). pp. 7738-7739. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170222-075015251

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja061853fDOIArticle
http://pubs.acs.org/doi/suppl/10.1021/ja061853fRelated ItemSupporting Information
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
Johnson and JohnsonUNSPECIFIED
Bristol-Myers SquibbUNSPECIFIED
MerckUNSPECIFIED
AmgenUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Issue or Number:24
Record Number:CaltechAUTHORS:20170222-075015251
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170222-075015251
Official Citation:The Catalytic Enantioselective, Protecting Group-Free Total Synthesis of (+)-Dichroanone Ryan M. McFadden and Brian M. Stoltz Journal of the American Chemical Society 2006 128 (24), 7738-7739 DOI: 10.1021/ja061853f
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:74448
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:22 Feb 2017 19:47
Last Modified:15 Jun 2020 20:07

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