Total Synthesis of (−)‐Indoxamycins A and B
The concise total syntheses of (−)‐indoxamycins A and B is reported. The chemistry features a seven‐step preparation of a highly congested [5.5.6] tricyclic advanced common intermediate from a readily available R‐carvone derivative. Key steps involve a Pauson–Khand reaction for the rapid constructio...
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| Published in | Angewandte Chemie Vol. 131; no. 20; pp. 6731 - 6734 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
Wiley Subscription Services, Inc
13.05.2019
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| Subjects | |
| Online Access | Get full text |
| ISSN | 0044-8249 1521-3757 |
| DOI | 10.1002/ange.201902043 |
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| Abstract | The concise total syntheses of (−)‐indoxamycins A and B is reported. The chemistry features a seven‐step preparation of a highly congested [5.5.6] tricyclic advanced common intermediate from a readily available R‐carvone derivative. Key steps involve a Pauson–Khand reaction for the rapid construction of a basic scaffold bearing a quaternary carbon, a copper‐catalyzed Michael addition for the introduction of another adjacent all‐carbon quaternary stereocenter, and a tandem retro‐oxa‐Michael addition/1,2‐addition/oxa‐Michael addition for the installation of a trisubstituted olefin side chain. This synthetic strategy allows for easy access to both enantiomers of this family of natural products and their analogues from cost‐effective starting material through straightforward chemical transformations.
Die Totalsynthese von (−)‐Indoxamycin A und B beinhaltet eine Pauson‐Khand‐Reaktion, eine Tandemreaktion aus Retro‐Oxa‐Michael‐Addition, 1,2‐Addition und Oxa‐Michael‐Addition und eine Mukaiyama‐Aldolreaktion. Somit lässt sich in sieben Schritten aus einem R‐Carvon‐Derivat ein gemeinsames tricyclisches Intermediat generieren, aus dem wiederum in sechs oder neun Schritten die Synthese von (−)‐Indoxamycin A und B erfolgt. |
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| AbstractList | The concise total syntheses of (−)‐indoxamycins A and B is reported. The chemistry features a seven‐step preparation of a highly congested [5.5.6] tricyclic advanced common intermediate from a readily available R‐carvone derivative. Key steps involve a Pauson–Khand reaction for the rapid construction of a basic scaffold bearing a quaternary carbon, a copper‐catalyzed Michael addition for the introduction of another adjacent all‐carbon quaternary stereocenter, and a tandem retro‐oxa‐Michael addition/1,2‐addition/oxa‐Michael addition for the installation of a trisubstituted olefin side chain. This synthetic strategy allows for easy access to both enantiomers of this family of natural products and their analogues from cost‐effective starting material through straightforward chemical transformations.
Die Totalsynthese von (−)‐Indoxamycin A und B beinhaltet eine Pauson‐Khand‐Reaktion, eine Tandemreaktion aus Retro‐Oxa‐Michael‐Addition, 1,2‐Addition und Oxa‐Michael‐Addition und eine Mukaiyama‐Aldolreaktion. Somit lässt sich in sieben Schritten aus einem R‐Carvon‐Derivat ein gemeinsames tricyclisches Intermediat generieren, aus dem wiederum in sechs oder neun Schritten die Synthese von (−)‐Indoxamycin A und B erfolgt. The concise total syntheses of (−)‐indoxamycins A and B is reported. The chemistry features a seven‐step preparation of a highly congested [5.5.6] tricyclic advanced common intermediate from a readily available R‐carvone derivative. Key steps involve a Pauson–Khand reaction for the rapid construction of a basic scaffold bearing a quaternary carbon, a copper‐catalyzed Michael addition for the introduction of another adjacent all‐carbon quaternary stereocenter, and a tandem retro‐oxa‐Michael addition/1,2‐addition/oxa‐Michael addition for the installation of a trisubstituted olefin side chain. This synthetic strategy allows for easy access to both enantiomers of this family of natural products and their analogues from cost‐effective starting material through straightforward chemical transformations. The concise total syntheses of (−)‐indoxamycins A and B is reported. The chemistry features a seven‐step preparation of a highly congested [5.5.6] tricyclic advanced common intermediate from a readily available R ‐carvone derivative. Key steps involve a Pauson–Khand reaction for the rapid construction of a basic scaffold bearing a quaternary carbon, a copper‐catalyzed Michael addition for the introduction of another adjacent all‐carbon quaternary stereocenter, and a tandem retro‐oxa‐Michael addition/1,2‐addition/oxa‐Michael addition for the installation of a trisubstituted olefin side chain. This synthetic strategy allows for easy access to both enantiomers of this family of natural products and their analogues from cost‐effective starting material through straightforward chemical transformations. |
| Author | Hu, Naifeng Liang, Guangxin Dong, Changming Zhang, Cuifang |
| Author_xml | – sequence: 1 givenname: Naifeng orcidid: 0000-0001-8385-7410 surname: Hu fullname: Hu, Naifeng organization: Nankai University – sequence: 2 givenname: Changming surname: Dong fullname: Dong, Changming organization: Nankai University – sequence: 3 givenname: Cuifang surname: Zhang fullname: Zhang, Cuifang organization: Nankai University – sequence: 4 givenname: Guangxin orcidid: 0000-0003-3122-0332 surname: Liang fullname: Liang, Guangxin email: lianggx@nankai.edu.cn organization: Nankai University |
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| Snippet | The concise total syntheses of (−)‐indoxamycins A and B is reported. The chemistry features a seven‐step preparation of a highly congested [5.5.6] tricyclic... |
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| SubjectTerms | Carbon Carvone Chemistry Cycloaddition Enantiomers Indoxamycine Natural products Organic chemistry Polyketide Tandemreaktionen Totalsynthese |
| Title | Total Synthesis of (−)‐Indoxamycins A and B |
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