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. doi:10.1021/ja061853f. 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:

URL	URL Type	Description
http://dx.doi.org/10.1021/ja061853f	DOI	Article
http://pubs.acs.org/doi/suppl/10.1021/ja061853f	Related Item	Supporting Information

ORCID:

Author	ORCID
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 Agency	Grant Number
Johnson and Johnson	UNSPECIFIED
Bristol-Myers Squibb	UNSPECIFIED
Merck	UNSPECIFIED
Amgen	UNSPECIFIED
Camille and Henry Dreyfus Foundation	UNSPECIFIED

Issue or Number:

DOI:

10.1021/ja061853f

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

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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:

11 Nov 2021 05:27

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