A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids
Building cycles: A strategy for the concise, stereoselective synthesis of aspidosperma alkaloids and related structures via a common putative diiminium ion intermediate is reported. The approach enables the dimerization of aspidosperma-type structures at the sterically hindered C2 position. The inte...
| Main Authors: | , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Language: | en_US |
| Published: |
Wiley Blackwell
2013
|
| Online Access: | http://hdl.handle.net/1721.1/82466 https://orcid.org/0000-0003-3080-1063 |
| _version_ | 1826189248732069888 |
|---|---|
| author | Medley, Jonathan William Movassaghi, Mohammad |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Medley, Jonathan William Movassaghi, Mohammad |
| author_sort | Medley, Jonathan William |
| collection | MIT |
| description | Building cycles: A strategy for the concise, stereoselective synthesis of aspidosperma alkaloids and related structures via a common putative diiminium ion intermediate is reported. The approach enables the dimerization of aspidosperma-type structures at the sterically hindered C2 position. The intermediate is prepared in one step from the shown lactam through an electrophilic double-cyclization cascade (see scheme; Tf=trifluoromethanesulfonyl). |
| first_indexed | 2024-09-23T08:11:49Z |
| format | Article |
| id | mit-1721.1/82466 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T08:11:49Z |
| publishDate | 2013 |
| publisher | Wiley Blackwell |
| record_format | dspace |
| spelling | mit-1721.1/824662022-09-23T11:32:02Z A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids Medley, Jonathan William Movassaghi, Mohammad Massachusetts Institute of Technology. Department of Chemistry Medley, Jonathan William Movassaghi, Mohammad Building cycles: A strategy for the concise, stereoselective synthesis of aspidosperma alkaloids and related structures via a common putative diiminium ion intermediate is reported. The approach enables the dimerization of aspidosperma-type structures at the sterically hindered C2 position. The intermediate is prepared in one step from the shown lactam through an electrophilic double-cyclization cascade (see scheme; Tf=trifluoromethanesulfonyl). National Institute of General Medical Sciences (U.S.) (GM074825) 2013-11-18T20:32:57Z 2013-11-18T20:32:57Z 2012-05 201-01 Article http://purl.org/eprint/type/JournalArticle 14337851 1521-3773 http://hdl.handle.net/1721.1/82466 Medley, Jonathan William, and Mohammad Movassaghi. “A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids.” Angewandte Chemie International Edition 51, no. 19 (May 7, 2012): 4572-4576. https://orcid.org/0000-0003-3080-1063 en_US http://dx.doi.org/10.1002/anie.201200387 Angewandte Chemie International Edition Creative Commons Attribution-Noncommercial-Share Alike 3.0 http://creativecommons.org/licenses/by-nc-sa/3.0/ application/pdf Wiley Blackwell PMC |
| spellingShingle | Medley, Jonathan William Movassaghi, Mohammad A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids |
| title | A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids |
| title_full | A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids |
| title_fullStr | A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids |
| title_full_unstemmed | A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids |
| title_short | A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids |
| title_sort | concise and versatile double cyclization strategy for the highly stereoselective synthesis and arylative dimerization of aspidosperma alkaloids |
| url | http://hdl.handle.net/1721.1/82466 https://orcid.org/0000-0003-3080-1063 |
| work_keys_str_mv | AT medleyjonathanwilliam aconciseandversatiledoublecyclizationstrategyforthehighlystereoselectivesynthesisandarylativedimerizationofaspidospermaalkaloids AT movassaghimohammad aconciseandversatiledoublecyclizationstrategyforthehighlystereoselectivesynthesisandarylativedimerizationofaspidospermaalkaloids AT medleyjonathanwilliam conciseandversatiledoublecyclizationstrategyforthehighlystereoselectivesynthesisandarylativedimerizationofaspidospermaalkaloids AT movassaghimohammad conciseandversatiledoublecyclizationstrategyforthehighlystereoselectivesynthesisandarylativedimerizationofaspidospermaalkaloids |