Carbene-catalyzed formal [5 + 5] reaction for coumarin construction and total synthesis of defucogilvocarcins
An N-heterocyclic carbene-catalyzed formal [5 + 5] reaction between enals and furanones that generates multisubstituted coumarins in a single step is reported. Five atoms in each of the substrates are involved in this catalytic process to form a benzene and a lactone ring. The power of the method is...
| Main Authors: | , , , , , , |
|---|---|
| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2020
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/138310 |
| _version_ | 1826124682915479552 |
|---|---|
| author | Huang, Xuan Zhu, Tingshun Huang, Zhijian Zhang, Yuexia Jin, Zhichao Zanoni, Giuseppe Chi, Robin Yonggui |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Huang, Xuan Zhu, Tingshun Huang, Zhijian Zhang, Yuexia Jin, Zhichao Zanoni, Giuseppe Chi, Robin Yonggui |
| author_sort | Huang, Xuan |
| collection | NTU |
| description | An N-heterocyclic carbene-catalyzed formal [5 + 5] reaction between enals and furanones that generates multisubstituted coumarins in a single step is reported. Five atoms in each of the substrates are involved in this catalytic process to form a benzene and a lactone ring. The power of the method is further demonstrated in metal-free total syntheses of several natural products (defucogilvocarcins M, E, and V) bearing coumarin as the key structural motif. |
| first_indexed | 2024-10-01T06:24:41Z |
| format | Journal Article |
| id | ntu-10356/138310 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:24:41Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1383102023-02-28T19:50:43Z Carbene-catalyzed formal [5 + 5] reaction for coumarin construction and total synthesis of defucogilvocarcins Huang, Xuan Zhu, Tingshun Huang, Zhijian Zhang, Yuexia Jin, Zhichao Zanoni, Giuseppe Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry Chemical Response Aromatic Compounds An N-heterocyclic carbene-catalyzed formal [5 + 5] reaction between enals and furanones that generates multisubstituted coumarins in a single step is reported. Five atoms in each of the substrates are involved in this catalytic process to form a benzene and a lactone ring. The power of the method is further demonstrated in metal-free total syntheses of several natural products (defucogilvocarcins M, E, and V) bearing coumarin as the key structural motif. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2020-05-02T05:01:25Z 2020-05-02T05:01:25Z 2017 Journal Article Huang, X., Zhu, T., Huang, Z., Zhang, Y., Jin, Z., Zanoni, G., & Chi, R. Y. (2017). Carbene-catalyzed formal [5 + 5] reaction for coumarin construction and total synthesis of defucogilvocarcins. Organic letters, 19(22), 6188-6191. doi:10.1021/acs.orglett.7b03102 1523-7060 https://hdl.handle.net/10356/138310 10.1021/acs.orglett.7b03102 29111757 2-s2.0-85034615985 22 19 6188 6191 en Organic letters © 2017 American Chemical Society. All rights reserved. This paper was published in Organic letters and is made available with permission of American Chemical Society. application/pdf |
| spellingShingle | Science::Chemistry::Organic chemistry Chemical Response Aromatic Compounds Huang, Xuan Zhu, Tingshun Huang, Zhijian Zhang, Yuexia Jin, Zhichao Zanoni, Giuseppe Chi, Robin Yonggui Carbene-catalyzed formal [5 + 5] reaction for coumarin construction and total synthesis of defucogilvocarcins |
| title | Carbene-catalyzed formal [5 + 5] reaction for coumarin construction and total synthesis of defucogilvocarcins |
| title_full | Carbene-catalyzed formal [5 + 5] reaction for coumarin construction and total synthesis of defucogilvocarcins |
| title_fullStr | Carbene-catalyzed formal [5 + 5] reaction for coumarin construction and total synthesis of defucogilvocarcins |
| title_full_unstemmed | Carbene-catalyzed formal [5 + 5] reaction for coumarin construction and total synthesis of defucogilvocarcins |
| title_short | Carbene-catalyzed formal [5 + 5] reaction for coumarin construction and total synthesis of defucogilvocarcins |
| title_sort | carbene catalyzed formal 5 5 reaction for coumarin construction and total synthesis of defucogilvocarcins |
| topic | Science::Chemistry::Organic chemistry Chemical Response Aromatic Compounds |
| url | https://hdl.handle.net/10356/138310 |
| work_keys_str_mv | AT huangxuan carbenecatalyzedformal55reactionforcoumarinconstructionandtotalsynthesisofdefucogilvocarcins AT zhutingshun carbenecatalyzedformal55reactionforcoumarinconstructionandtotalsynthesisofdefucogilvocarcins AT huangzhijian carbenecatalyzedformal55reactionforcoumarinconstructionandtotalsynthesisofdefucogilvocarcins AT zhangyuexia carbenecatalyzedformal55reactionforcoumarinconstructionandtotalsynthesisofdefucogilvocarcins AT jinzhichao carbenecatalyzedformal55reactionforcoumarinconstructionandtotalsynthesisofdefucogilvocarcins AT zanonigiuseppe carbenecatalyzedformal55reactionforcoumarinconstructionandtotalsynthesisofdefucogilvocarcins AT chirobinyonggui carbenecatalyzedformal55reactionforcoumarinconstructionandtotalsynthesisofdefucogilvocarcins |