New Catalytic Methods for the Preparation of Tryptophans and Pyrroloindolines: Total Synthesis of (+)-Naseseazines A and B and (–)-Aspergilazine A

<p>Tryptophan and unnatural tryptophan derivatives are important building blocks for the total synthesis of natural products, as well as the development of new drugs, biological probes, and chiral small molecule catalysts. This thesis describes various catalytic methods for the preparation of...

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Main Author:	Kieffer, Madeleine Eileen
Format:	Others
Published:	2015
Online Access:	https://thesis.library.caltech.edu/8999/1/MEK_Thesis_Final.pdf https://thesis.library.caltech.edu/8999/7/title%20page%20etc.pdf https://thesis.library.caltech.edu/8999/13/Chapter%201.pdf https://thesis.library.caltech.edu/8999/19/Chapter%202-Final.pdf https://thesis.library.caltech.edu/8999/25/Chapter%203-Final.pdf https://thesis.library.caltech.edu/8999/31/Chapter%204%20-%20Final.pdf Kieffer, Madeleine Eileen (2015) New Catalytic Methods for the Preparation of Tryptophans and Pyrroloindolines: Total Synthesis of (+)-Naseseazines A and B and (–)-Aspergilazine A. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/Z9X0650X. https://resolver.caltech.edu/CaltechTHESIS:06052015-132556787 <https://resolver.caltech.edu/CaltechTHESIS:06052015-132556787>

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spelling	ndltd-CALTECH-oai-thesis.library.caltech.edu-89992019-10-05T03:03:37Z New Catalytic Methods for the Preparation of Tryptophans and Pyrroloindolines: Total Synthesis of (+)-Naseseazines A and B and (–)-Aspergilazine A Kieffer, Madeleine Eileen <p>Tryptophan and unnatural tryptophan derivatives are important building blocks for the total synthesis of natural products, as well as the development of new drugs, biological probes, and chiral small molecule catalysts. This thesis describes various catalytic methods for the preparation of tryptophan derivatives as well as their functionalization and use in natural product total synthesis.</p> <p>Herein, the tandem Friedel–Crafts conjugate addition/asymmetric protonation reaction between 2-substituted indoles and methyl 2-acetamidoacrylate to provide enantioenriched trytophans is reported. This method inspired further work in the area of transition metal catalyzed arylation reactions. We report the development of the coppercatalyzed arylation of tryptamine and tryptophan derivatives. The utility of these transformations is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B. Further work on the development of a mild and general Larock indolization protocol to access unnatural tryptophans is also discussed.</p> 2015 Thesis NonPeerReviewed application/pdf https://thesis.library.caltech.edu/8999/1/MEK_Thesis_Final.pdf application/pdf https://thesis.library.caltech.edu/8999/7/title%20page%20etc.pdf application/pdf https://thesis.library.caltech.edu/8999/13/Chapter%201.pdf application/pdf https://thesis.library.caltech.edu/8999/19/Chapter%202-Final.pdf application/pdf https://thesis.library.caltech.edu/8999/25/Chapter%203-Final.pdf application/pdf https://thesis.library.caltech.edu/8999/31/Chapter%204%20-%20Final.pdf https://resolver.caltech.edu/CaltechTHESIS:06052015-132556787 Kieffer, Madeleine Eileen (2015) New Catalytic Methods for the Preparation of Tryptophans and Pyrroloindolines: Total Synthesis of (+)-Naseseazines A and B and (–)-Aspergilazine A. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/Z9X0650X. https://resolver.caltech.edu/CaltechTHESIS:06052015-132556787 <https://resolver.caltech.edu/CaltechTHESIS:06052015-132556787> https://thesis.library.caltech.edu/8999/
collection	NDLTD
format	Others
sources	NDLTD
description	<p>Tryptophan and unnatural tryptophan derivatives are important building blocks for the total synthesis of natural products, as well as the development of new drugs, biological probes, and chiral small molecule catalysts. This thesis describes various catalytic methods for the preparation of tryptophan derivatives as well as their functionalization and use in natural product total synthesis.</p> <p>Herein, the tandem Friedel–Crafts conjugate addition/asymmetric protonation reaction between 2-substituted indoles and methyl 2-acetamidoacrylate to provide enantioenriched trytophans is reported. This method inspired further work in the area of transition metal catalyzed arylation reactions. We report the development of the coppercatalyzed arylation of tryptamine and tryptophan derivatives. The utility of these transformations is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B. Further work on the development of a mild and general Larock indolization protocol to access unnatural tryptophans is also discussed.</p>
author	Kieffer, Madeleine Eileen
spellingShingle	Kieffer, Madeleine Eileen New Catalytic Methods for the Preparation of Tryptophans and Pyrroloindolines: Total Synthesis of (+)-Naseseazines A and B and (–)-Aspergilazine A
author_facet	Kieffer, Madeleine Eileen
author_sort	Kieffer, Madeleine Eileen
title	New Catalytic Methods for the Preparation of Tryptophans and Pyrroloindolines: Total Synthesis of (+)-Naseseazines A and B and (–)-Aspergilazine A
title_short	New Catalytic Methods for the Preparation of Tryptophans and Pyrroloindolines: Total Synthesis of (+)-Naseseazines A and B and (–)-Aspergilazine A
title_full	New Catalytic Methods for the Preparation of Tryptophans and Pyrroloindolines: Total Synthesis of (+)-Naseseazines A and B and (–)-Aspergilazine A
title_fullStr	New Catalytic Methods for the Preparation of Tryptophans and Pyrroloindolines: Total Synthesis of (+)-Naseseazines A and B and (–)-Aspergilazine A
title_full_unstemmed	New Catalytic Methods for the Preparation of Tryptophans and Pyrroloindolines: Total Synthesis of (+)-Naseseazines A and B and (–)-Aspergilazine A
title_sort	new catalytic methods for the preparation of tryptophans and pyrroloindolines: total synthesis of (+)-naseseazines a and b and (–)-aspergilazine a
publishDate	2015
url	https://thesis.library.caltech.edu/8999/1/MEK_Thesis_Final.pdf https://thesis.library.caltech.edu/8999/7/title%20page%20etc.pdf https://thesis.library.caltech.edu/8999/13/Chapter%201.pdf https://thesis.library.caltech.edu/8999/19/Chapter%202-Final.pdf https://thesis.library.caltech.edu/8999/25/Chapter%203-Final.pdf https://thesis.library.caltech.edu/8999/31/Chapter%204%20-%20Final.pdf Kieffer, Madeleine Eileen (2015) New Catalytic Methods for the Preparation of Tryptophans and Pyrroloindolines: Total Synthesis of (+)-Naseseazines A and B and (–)-Aspergilazine A. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/Z9X0650X. https://resolver.caltech.edu/CaltechTHESIS:06052015-132556787 <https://resolver.caltech.edu/CaltechTHESIS:06052015-132556787>
work_keys_str_mv	AT kieffermadeleineeileen newcatalyticmethodsforthepreparationoftryptophansandpyrroloindolinestotalsynthesisofnaseseazinesaandbandaspergilazinea
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New Catalytic Methods for the Preparation of Tryptophans and Pyrroloindolines: Total Synthesis of (+)-Naseseazines A and B and (–)-Aspergilazine A

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