The development of iterative and cascade methods for the rapid synthesis of ladder polyether natural products
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2005.
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| Other Authors: | |
| Format: | Thesis |
| Language: | eng |
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Massachusetts Institute of Technology
2006
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| Online Access: | http://hdl.handle.net/1721.1/32478 |
| _version_ | 1826207931515797504 |
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| author | Heffron, Timothy Paul |
| author2 | Timothy F. Jamison. |
| author_facet | Timothy F. Jamison. Heffron, Timothy Paul |
| author_sort | Heffron, Timothy Paul |
| collection | MIT |
| description | Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2005. |
| first_indexed | 2024-09-23T13:57:13Z |
| format | Thesis |
| id | mit-1721.1/32478 |
| institution | Massachusetts Institute of Technology |
| language | eng |
| last_indexed | 2024-09-23T13:57:13Z |
| publishDate | 2006 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/324782019-04-12T14:30:53Z The development of iterative and cascade methods for the rapid synthesis of ladder polyether natural products Heffron, Timothy Paul Timothy F. Jamison. Massachusetts Institute of Technology. Dept. of Chemistry. Massachusetts Institute of Technology. Dept. of Chemistry. Chemistry. Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2005. MIT Science Library copy: Issued in leaves, in a 2 v. set. Also issued in leaves, in a 2 v. set. Vita. Includes bibliographical references . I. The Development of Methods for the Iterative Synthesis of Polytetrahydropyrans An iterative method comprising chain homologation, epoxidation, 6-endo cyclization, and protiodesilylation was developed. Notable achievements include the development of a novel propargyl organocopper coupling method, and the complete control of stereoselectivity and regioselectivity during the iterative synthesis of a tristetrahydropyran. The synthesis of the tristetrahydropyran was achieved in 18 total operations. ... (1) homologation (2) epoxidation (3) cyclization (4) protiodesilylation ... II. The Development of a Cascade Synthesis of Polytetrahydropyrans with No Directing Groups at Ring Junctions Cascade approaches to trans-fused tetrahydropyrans were studied. After exploring acid-promoted cascade cyclizations of polyepoxysilanes and polyepoxides without directing groups, the base-promoted cascade cyclization of polyepoxysilanes was realized. In this method, as many as five operations take place in a single step to provide a tristetrahydropyran with no directing groups at any ring junctions. The synthesis of the tristetrahydropyran was accomplished in 11 steps. ... by Timothy Paul Heffron. Ph.D. 2006-03-29T18:48:11Z 2006-03-29T18:48:11Z 2005 2005 Thesis http://hdl.handle.net/1721.1/32478 61772167 eng M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission. http://dspace.mit.edu/handle/1721.1/7582 311 p. 10240856 bytes 10262354 bytes application/pdf application/pdf application/pdf Massachusetts Institute of Technology |
| spellingShingle | Chemistry. Heffron, Timothy Paul The development of iterative and cascade methods for the rapid synthesis of ladder polyether natural products |
| title | The development of iterative and cascade methods for the rapid synthesis of ladder polyether natural products |
| title_full | The development of iterative and cascade methods for the rapid synthesis of ladder polyether natural products |
| title_fullStr | The development of iterative and cascade methods for the rapid synthesis of ladder polyether natural products |
| title_full_unstemmed | The development of iterative and cascade methods for the rapid synthesis of ladder polyether natural products |
| title_short | The development of iterative and cascade methods for the rapid synthesis of ladder polyether natural products |
| title_sort | development of iterative and cascade methods for the rapid synthesis of ladder polyether natural products |
| topic | Chemistry. |
| url | http://hdl.handle.net/1721.1/32478 |
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