Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

Pd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of “classic” natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenter...

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Main Authors:	Yiyang Liu, Marc Liniger, Ryan M. McFadden, Jenny L. Roizen, Jacquie Malette, Corey M. Reeves, Douglas C. Behenna, Masaki Seto, Jimin Kim, Justin T. Mohr, Scott C. Virgil, Brian M. Stoltz
Format:	Article
Language:	English
Published:	Beilstein-Institut 2014-10-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	enantioselective alkylation natural products palladium
Online Access:	https://doi.org/10.3762/bjoc.10.261

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spelling	doaj-53aff6b2b8524eb8bcb18875eaef6ba12021-02-02T01:06:59ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-10-011012501251210.3762/bjoc.10.2611860-5397-10-261Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylationYiyang Liu0Marc Liniger1Ryan M. McFadden2Jenny L. Roizen3Jacquie Malette4Corey M. Reeves5Douglas C. Behenna6Masaki Seto7Jimin Kim8Justin T. Mohr9Scott C. Virgil10Brian M. Stoltz11Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, Pasadena, CA, USAWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, Pasadena, CA, USAWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, Pasadena, CA, USAWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, Pasadena, CA, USAWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, Pasadena, CA, USAWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, Pasadena, CA, USAWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, Pasadena, CA, USAWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, Pasadena, CA, USAWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, Pasadena, CA, USAWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, Pasadena, CA, USAWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, Pasadena, CA, USAWarren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, Pasadena, CA, USAPd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of “classic” natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenters to address the synthetic hurdles encountered over many decades across multiple compound classes spanning carbohydrate derivatives, terpenes, and alkaloids. These enantioselective methods will impact both academic and industrial settings, where the synthesis of stereogenic quaternary carbons is a continuing challenge.https://doi.org/10.3762/bjoc.10.261enantioselective alkylationnatural productspalladium
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Yiyang Liu Marc Liniger Ryan M. McFadden Jenny L. Roizen Jacquie Malette Corey M. Reeves Douglas C. Behenna Masaki Seto Jimin Kim Justin T. Mohr Scott C. Virgil Brian M. Stoltz
spellingShingle	Yiyang Liu Marc Liniger Ryan M. McFadden Jenny L. Roizen Jacquie Malette Corey M. Reeves Douglas C. Behenna Masaki Seto Jimin Kim Justin T. Mohr Scott C. Virgil Brian M. Stoltz Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation Beilstein Journal of Organic Chemistry enantioselective alkylation natural products palladium
author_facet	Yiyang Liu Marc Liniger Ryan M. McFadden Jenny L. Roizen Jacquie Malette Corey M. Reeves Douglas C. Behenna Masaki Seto Jimin Kim Justin T. Mohr Scott C. Virgil Brian M. Stoltz
author_sort	Yiyang Liu
title	Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation
title_short	Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation
title_full	Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation
title_fullStr	Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation
title_full_unstemmed	Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation
title_sort	formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2014-10-01
description	Pd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of “classic” natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenters to address the synthetic hurdles encountered over many decades across multiple compound classes spanning carbohydrate derivatives, terpenes, and alkaloids. These enantioselective methods will impact both academic and industrial settings, where the synthesis of stereogenic quaternary carbons is a continuing challenge.
topic	enantioselective alkylation natural products palladium
url	https://doi.org/10.3762/bjoc.10.261
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Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

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