Enantioselective Alkoxycyclization of 1,6‐Enynes with Gold(I)‐Cavitands: Total Synthesis of Mafaicheenamine C
Chiral gold(I)-cavitand complexes have been developed for the enantioselective alkoxycyclization of 1,6-enynes. This enantioselective cyclization has been applied for the first total synthesis of carbazole alkaloid (+)-mafaicheenamine C and its enantiomer, establishing its configuration as R. The ca...
| Authors: | ; ; ; ; |
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| Format: | Article |
| Status: | Accepted version |
| Publication date: | 2021 |
| Country: | España |
| Institution: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repository: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:2072/449890 |
| Online Access: | http://hdl.handle.net/2072/449890 https://doi.org/10.1002/anie.202017035 |
| Access Level: | Open access |
| Keyword: | 54 |
| _version_ | 1878738007480074240 |
|---|---|
| author | Martín-Torres, Inmaculada |
| author2 | Ogalla, Gala Yang, Jin-Ming Rinaldi, Antonia Echavarren, Antonio M. |
| author2_role | author author author author |
| author_browse | Echavarren, Antonio M. Martín-Torres, Inmaculada Ogalla, Gala Rinaldi, Antonia Yang, Jin-Ming |
| author_facet | Martín-Torres, Inmaculada Ogalla, Gala Yang, Jin-Ming Rinaldi, Antonia Echavarren, Antonio M. |
| author_role | author |
| collection | Recercat. Dipósit de la Recerca de Catalunya |
| description | Chiral gold(I)-cavitand complexes have been developed for the enantioselective alkoxycyclization of 1,6-enynes. This enantioselective cyclization has been applied for the first total synthesis of carbazole alkaloid (+)-mafaicheenamine C and its enantiomer, establishing its configuration as R. The cavity effect was also evaluated in the cycloisomerization of dienynes. A combination of experiments and theoretical studies demonstrates that the cavity of the gold(I) complexes forces the enynes to adopt constrained conformations, which results in the high observed regio- and stereoselectivities. |
| eu_rights_str_mv | openAccess |
| format | article |
| id | ES_a8458ae18dbc4b236368fa0d99d4e155 |
| institution | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| instname_str | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| network_acronym_str | ES |
| network_name_str | España |
| oai_identifier_str | oai:recercat.cat:2072/449890 |
| publishDate | 2021 |
| publishDateSort | 2021 |
| reponame_str | Recercat. Dipósit de la Recerca de Catalunya |
| spelling | Enantioselective Alkoxycyclization of 1,6‐Enynes with Gold(I)‐Cavitands: Total Synthesis of Mafaicheenamine C Martín-Torres, Inmaculada Ogalla, Gala Yang, Jin-Ming Rinaldi, Antonia Echavarren, Antonio M. 54 Chiral gold(I)-cavitand complexes have been developed for the enantioselective alkoxycyclization of 1,6-enynes. This enantioselective cyclization has been applied for the first total synthesis of carbazole alkaloid (+)-mafaicheenamine C and its enantiomer, establishing its configuration as R. The cavity effect was also evaluated in the cycloisomerization of dienynes. A combination of experiments and theoretical studies demonstrates that the cavity of the gold(I) complexes forces the enynes to adopt constrained conformations, which results in the high observed regio- and stereoselectivities. http://hdl.handle.net/2072/449890 https://doi.org/10.1002/anie.202017035 |
| spellingShingle | Enantioselective Alkoxycyclization of 1,6‐Enynes with Gold(I)‐Cavitands: Total Synthesis of Mafaicheenamine C Martín-Torres, Inmaculada 54 |
| status_str | acceptedVersion |
| title | Enantioselective Alkoxycyclization of 1,6‐Enynes with Gold(I)‐Cavitands: Total Synthesis of Mafaicheenamine C |
| title_full | Enantioselective Alkoxycyclization of 1,6‐Enynes with Gold(I)‐Cavitands: Total Synthesis of Mafaicheenamine C |
| title_fullStr | Enantioselective Alkoxycyclization of 1,6‐Enynes with Gold(I)‐Cavitands: Total Synthesis of Mafaicheenamine C |
| title_full_unstemmed | Enantioselective Alkoxycyclization of 1,6‐Enynes with Gold(I)‐Cavitands: Total Synthesis of Mafaicheenamine C |
| title_short | Enantioselective Alkoxycyclization of 1,6‐Enynes with Gold(I)‐Cavitands: Total Synthesis of Mafaicheenamine C |
| title_sort | Enantioselective Alkoxycyclization of 1,6‐Enynes with Gold(I)‐Cavitands: Total Synthesis of Mafaicheenamine C |
| topic | 54 |
| topic_facet | 54 |
| url | http://hdl.handle.net/2072/449890 https://doi.org/10.1002/anie.202017035 |