A Concise Approach to Paxilline Indole Diterpenes
A synthetic approach to paxilline indole diterpenes is described. The route to the pentacyclic core relies on a new regioselective alkenylation of ketones and a tandem radical addition–aldol reaction sequence to access vicinal quaternary stereocenters. Emindole SB, the simplest member of the fam...
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| Published in | Journal of the American Chemical Society Vol. 137; no. 49; pp. 15410 - 15413 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
16.12.2015
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | A synthetic approach to paxilline indole diterpenes is described. The route to the pentacyclic core relies on a new regioselective alkenylation of ketones and a tandem radical addition–aldol reaction sequence to access vicinal quaternary stereocenters. Emindole SB, the simplest member of the family, is synthesized in 11 steps from commercially available material to demonstrate the application of this approach. |
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| AbstractList | A synthetic approach to paxilline indole diterpenes is described. The route to the pentacyclic core relies on a new regioselective alkenylation of ketones and a tandem radical addition-aldol reaction sequence to access vicinal quaternary stereocenters. Emindole SB, the simplest member of the family, is synthesized in 11 steps from commercially available material to demonstrate the application of this approach. A synthetic approach to paxilline indole diterpenes is described. The route to the pentacyclic core relies on a new regioselective alkenylation of ketones and a tandem radical addition–aldol reaction sequence to access vicinal quaternary stereocenters. Emindole SB, the simplest member of the family, is synthesized in 11 steps from commercially available material to demonstrate the application of this approach. A synthetic approach to paxilline indole diterpenes is described. The route to the pentacyclic core relies on a new regioselective alkenylation of ketones and a tandem radical addition-aldol reaction sequence to access vicinal quaternary stereocenters. Emindole SB, the simplest member of the family, is synthesized in 11 steps from commercially available material to demonstrate the application of this approach.A synthetic approach to paxilline indole diterpenes is described. The route to the pentacyclic core relies on a new regioselective alkenylation of ketones and a tandem radical addition-aldol reaction sequence to access vicinal quaternary stereocenters. Emindole SB, the simplest member of the family, is synthesized in 11 steps from commercially available material to demonstrate the application of this approach. A synthetic approach to paxilline indole diterpenes is described. The route to the pentacyclic core relies on a new regioselective alkenylation of ketones and a tandem radical addition−aldol reaction sequence to access vicinal quaternary stereocenters. Emindole SB, the simplest member of the family, is synthesized in 11 steps from commercially available material to demonstrate the application of this approach. A synthetic approach to paxilline indole diterpenes is described. The route to the pentacydic core relies on a new regioselective alkenylation of ketones and a tandem radical addition-aldol reaction sequence to access vicinal quaternary stereocenters. Emindole SB, the simplest member of the family, is synthesized in 11 steps from commercially available material to demonstrate the application of this approach. |
| Author | Pronin, Sergey V Kuenstner, Eric J George, David T |
| AuthorAffiliation | Department of Chemistry University of California |
| AuthorAffiliation_xml | – name: University of California – name: Department of Chemistry |
| Author_xml | – sequence: 1 givenname: David T surname: George fullname: George, David T – sequence: 2 givenname: Eric J surname: Kuenstner fullname: Kuenstner, Eric J – sequence: 3 givenname: Sergey V surname: Pronin fullname: Pronin, Sergey V email: spronin@uci.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26593869$$D View this record in MEDLINE/PubMed |
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| Snippet | A synthetic approach to paxilline indole diterpenes is described. The route to the pentacyclic core relies on a new regioselective alkenylation of ketones... A synthetic approach to paxilline indole diterpenes is described. The route to the pentacydic core relies on a new regioselective alkenylation of ketones and a... A synthetic approach to paxilline indole diterpenes is described. The route to the pentacyclic core relies on a new regioselective alkenylation of ketones and... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary Diterpenes - chemistry diterpenoids Indoles - chemistry ketones Molecular Structure paxilline Physical Sciences Science & Technology Terpenes - chemistry |
| Title | A Concise Approach to Paxilline Indole Diterpenes |
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