Collective Total Synthesis of Aspidofractinine Alkaloids through the Development of a Bischler–Napieralski/Semipinacol Rearrangement Reaction
A tandem Bischler–Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a privileged structural unit of aspidofractinine‐type monoterpenoid indole alkaloids, and was used in combination with a subsequent Mannich reaction...
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| Published in | Angewandte Chemie International Edition Vol. 59; no. 49; pp. 21954 - 21958 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
01.12.2020
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| Edition | International ed. in English |
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| Abstract | A tandem Bischler–Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a privileged structural unit of aspidofractinine‐type monoterpenoid indole alkaloids, and was used in combination with a subsequent Mannich reaction to expeditiously construct the central bridged bicyclo[2.2.1]heptane ring system of these molecules with contiguous quaternary centers. The development of this novel strategy culminated in the collective total synthesis of four aspidofractinine alkaloids.
A tandem Bischler–Napieralski reaction and semipinacol rearrangement was combined with a subsequent Mannich reaction for the expeditious construction of the bicyclo[2.2.1]heptanone motif of four aspidofractinine alkaloids (see scheme). The strategy further highlights the synthetic potential of tandem semipinacol rearrangement reactions in assembling spirocyclic ring systems with a congested chemical environment. |
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| AbstractList | A tandem Bischler-Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a privileged structural unit of aspidofractinine-type monoterpenoid indole alkaloids, and was used in combination with a subsequent Mannich reaction to expeditiously construct the central bridged bicyclo[2.2.1]heptane ring system of these molecules with contiguous quaternary centers. The development of this novel strategy culminated in the collective total synthesis of four aspidofractinine alkaloids.A tandem Bischler-Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a privileged structural unit of aspidofractinine-type monoterpenoid indole alkaloids, and was used in combination with a subsequent Mannich reaction to expeditiously construct the central bridged bicyclo[2.2.1]heptane ring system of these molecules with contiguous quaternary centers. The development of this novel strategy culminated in the collective total synthesis of four aspidofractinine alkaloids. A tandem Bischler–Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a privileged structural unit of aspidofractinine‐type monoterpenoid indole alkaloids, and was used in combination with a subsequent Mannich reaction to expeditiously construct the central bridged bicyclo[2.2.1]heptane ring system of these molecules with contiguous quaternary centers. The development of this novel strategy culminated in the collective total synthesis of four aspidofractinine alkaloids. A tandem Bischler–Napieralski reaction and semipinacol rearrangement was combined with a subsequent Mannich reaction for the expeditious construction of the bicyclo[2.2.1]heptanone motif of four aspidofractinine alkaloids (see scheme). The strategy further highlights the synthetic potential of tandem semipinacol rearrangement reactions in assembling spirocyclic ring systems with a congested chemical environment. A tandem Bischler–Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a privileged structural unit of aspidofractinine‐type monoterpenoid indole alkaloids, and was used in combination with a subsequent Mannich reaction to expeditiously construct the central bridged bicyclo[2.2.1]heptane ring system of these molecules with contiguous quaternary centers. The development of this novel strategy culminated in the collective total synthesis of four aspidofractinine alkaloids. |
| Author | Wang, Shuang‐Hu Tu, Yong‐Qiang Zhang, Xiao‐Ming Zhuang, Qing‐Bo Guo, Xiang Zhang, Fu‐Min Ke, Tian Si, Rui‐Qi |
| Author_xml | – sequence: 1 givenname: Shuang‐Hu orcidid: 0000-0002-9040-3721 surname: Wang fullname: Wang, Shuang‐Hu organization: Lanzhou University – sequence: 2 givenname: Rui‐Qi surname: Si fullname: Si, Rui‐Qi organization: Lanzhou University – sequence: 3 givenname: Qing‐Bo surname: Zhuang fullname: Zhuang, Qing‐Bo organization: Lanzhou University – sequence: 4 givenname: Xiang surname: Guo fullname: Guo, Xiang organization: Lanzhou University – sequence: 5 givenname: Tian surname: Ke fullname: Ke, Tian organization: Shanghai Jiao Tong University – sequence: 6 givenname: Xiao‐Ming surname: Zhang fullname: Zhang, Xiao‐Ming email: zhangxiaom@lzu.edu.cn organization: Lanzhou University – sequence: 7 givenname: Fu‐Min surname: Zhang fullname: Zhang, Fu‐Min email: zhangfm@lzu.edu.cn organization: Lanzhou University – sequence: 8 givenname: Yong‐Qiang orcidid: 0000-0002-9784-4052 surname: Tu fullname: Tu, Yong‐Qiang email: tuyq@lzu.edu.cn organization: Shanghai Jiao Tong University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32851781$$D View this record in MEDLINE/PubMed |
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| Keywords | MONOTERPENOID INDOLE ALKALOIDS ACID domino reactions alkaloids semipinacol rearrangement total synthesis FACILE Bischler-Napieralski reaction |
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| Snippet | A tandem Bischler–Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a... A tandem Bischler-Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a... |
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| SubjectTerms | Alkaloids Bischler–Napieralski reaction Chemistry Chemistry, Multidisciplinary domino reactions Heptanes Indoles Physical Sciences Science & Technology semipinacol rearrangement Synthesis total synthesis |
| Title | Collective Total Synthesis of Aspidofractinine Alkaloids through the Development of a Bischler–Napieralski/Semipinacol Rearrangement Reaction |
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