Site‐Selective trans‐Hydrostannation of 1,3‐ and 1,n‐Diynes: Application to the Total Synthesis of Typhonosides E and F, and a Fluorinated Cerebroside Analogue
Propargyl alcohols are privileged substrates for stereochemically unorthodox trans‐hydrostannation reactions catalyzed by [Cp*RuCl]4 (Cp*=pentamethylcyclopentadienyl), because an incipient hydrogen bond between the ‐OH group and the polarized [Ru‐Cl] unit assists substrate binding. For this very rea...
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| Published in | Chemistry : a European journal Vol. 24; no. 38; pp. 9667 - 9674 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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05.07.2018
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| Abstract | Propargyl alcohols are privileged substrates for stereochemically unorthodox trans‐hydrostannation reactions catalyzed by [Cp*RuCl]4 (Cp*=pentamethylcyclopentadienyl), because an incipient hydrogen bond between the ‐OH group and the polarized [Ru‐Cl] unit assists substrate binding. For this very reason, it is also possible to subject diyne derivatives carrying one ‐OH group to site‐selective stannylation, even if the acetylene units are conjugated and hence, electronically coupled. An unusual temperature dependence was observed in that heating tends to improve site‐selectivity, whereas per‐stannylation is favored when the reaction is carried out in the cold. This counterintuitive trend can be rationalized based on spectroscopic data; additional support comes from the isolation of the unusual bimetallic complex 11. The bridging fulvene and enynyl ligands in 11 are thought to reflect an interligand redox isomerization process likely triggered by synchronous activation of the 1,3‐diyne substrate by two metal centers. The preparative relevance of site‐selective trans‐hydrostannation is illustrated by the total synthesis of two members of the typhonoside series of glycolipids, which are endowed with neuroprotective properties. Moreover, the preparation of a fluoroalkene sphingosine analogue shows that the tin residue also serves as a versatile handle for late‐stage modification of a bioactive target compound.
Counterintuitive: That the selectivity for site‐selective mono‐stannation increases at higher temperature is not obvious at first sight, but can be explained based on spectroscopic, computational, and crystallographic data. This transformation gained a strategic role in the total synthesis of two isomeric cerebroside derivatives and a non‐natural fluoro‐alkene analogue thereof. |
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| AbstractList | Propargyl alcohols are privileged substrates for stereochemically unorthodox
trans
‐hydrostannation reactions catalyzed by [Cp*RuCl]
4
(Cp*=pentamethylcyclopentadienyl), because an incipient hydrogen bond between the ‐OH group and the polarized [Ru‐Cl] unit assists substrate binding. For this very reason, it is also possible to subject diyne derivatives carrying one ‐OH group to site‐selective stannylation, even if the acetylene units are conjugated and hence, electronically coupled. An unusual temperature dependence was observed in that heating tends to improve site‐selectivity, whereas per‐stannylation is favored when the reaction is carried out in the cold. This counterintuitive trend can be rationalized based on spectroscopic data; additional support comes from the isolation of the unusual bimetallic complex
11
. The bridging fulvene and enynyl ligands in
11
are thought to reflect an interligand redox isomerization process likely triggered by synchronous activation of the 1,3‐diyne substrate by two metal centers. The preparative relevance of site‐selective
trans
‐hydrostannation is illustrated by the total synthesis of two members of the typhonoside series of glycolipids, which are endowed with neuroprotective properties. Moreover, the preparation of a fluoroalkene sphingosine analogue shows that the tin residue also serves as a versatile handle for late‐stage modification of a bioactive target compound. Propargyl alcohols are privileged substrates for stereochemically unorthodox trans-hydrostannation reactions catalyzed by [Cp*RuCl]4 (Cp*=pentamethylcyclopentadienyl), because an incipient hydrogen bond between the -OH group and the polarized [Ru-Cl] unit assists substrate binding. For this very reason, it is also possible to subject diyne derivatives carrying one -OH group to site-selective stannylation, even if the acetylene units are conjugated and hence, electronically coupled. An unusual temperature dependence was observed in that heating tends to improve site-selectivity, whereas per-stannylation is favored when the reaction is carried out in the cold. This counterintuitive trend can be rationalized based on spectroscopic data; additional support comes from the isolation of the unusual bimetallic complex 11. The bridging fulvene and enynyl ligands in 11 are thought to reflect an interligand redox isomerization process likely triggered by synchronous activation of the 1,3-diyne substrate by two metal centers. The preparative relevance of site-selective trans-hydrostannation is illustrated by the total synthesis of two members of the typhonoside series of glycolipids, which are endowed with neuroprotective properties. Moreover, the preparation of a fluoroalkene sphingosine analogue shows that the tin residue also serves as a versatile handle for late-stage modification of a bioactive target compound.Propargyl alcohols are privileged substrates for stereochemically unorthodox trans-hydrostannation reactions catalyzed by [Cp*RuCl]4 (Cp*=pentamethylcyclopentadienyl), because an incipient hydrogen bond between the -OH group and the polarized [Ru-Cl] unit assists substrate binding. For this very reason, it is also possible to subject diyne derivatives carrying one -OH group to site-selective stannylation, even if the acetylene units are conjugated and hence, electronically coupled. An unusual temperature dependence was observed in that heating tends to improve site-selectivity, whereas per-stannylation is favored when the reaction is carried out in the cold. This counterintuitive trend can be rationalized based on spectroscopic data; additional support comes from the isolation of the unusual bimetallic complex 11. The bridging fulvene and enynyl ligands in 11 are thought to reflect an interligand redox isomerization process likely triggered by synchronous activation of the 1,3-diyne substrate by two metal centers. The preparative relevance of site-selective trans-hydrostannation is illustrated by the total synthesis of two members of the typhonoside series of glycolipids, which are endowed with neuroprotective properties. Moreover, the preparation of a fluoroalkene sphingosine analogue shows that the tin residue also serves as a versatile handle for late-stage modification of a bioactive target compound. Propargyl alcohols are privileged substrates for stereochemically unorthodox trans‐hydrostannation reactions catalyzed by [Cp*RuCl]4 (Cp*=pentamethylcyclopentadienyl), because an incipient hydrogen bond between the ‐OH group and the polarized [Ru‐Cl] unit assists substrate binding. For this very reason, it is also possible to subject diyne derivatives carrying one ‐OH group to site‐selective stannylation, even if the acetylene units are conjugated and hence, electronically coupled. An unusual temperature dependence was observed in that heating tends to improve site‐selectivity, whereas per‐stannylation is favored when the reaction is carried out in the cold. This counterintuitive trend can be rationalized based on spectroscopic data; additional support comes from the isolation of the unusual bimetallic complex 11. The bridging fulvene and enynyl ligands in 11 are thought to reflect an interligand redox isomerization process likely triggered by synchronous activation of the 1,3‐diyne substrate by two metal centers. The preparative relevance of site‐selective trans‐hydrostannation is illustrated by the total synthesis of two members of the typhonoside series of glycolipids, which are endowed with neuroprotective properties. Moreover, the preparation of a fluoroalkene sphingosine analogue shows that the tin residue also serves as a versatile handle for late‐stage modification of a bioactive target compound. Counterintuitive: That the selectivity for site‐selective mono‐stannation increases at higher temperature is not obvious at first sight, but can be explained based on spectroscopic, computational, and crystallographic data. This transformation gained a strategic role in the total synthesis of two isomeric cerebroside derivatives and a non‐natural fluoro‐alkene analogue thereof. Propargyl alcohols are privileged substrates for stereochemically unorthodox trans-hydrostannation reactions catalyzed by [Cp*RuCl] (Cp*=pentamethylcyclopentadienyl), because an incipient hydrogen bond between the -OH group and the polarized [Ru-Cl] unit assists substrate binding. For this very reason, it is also possible to subject diyne derivatives carrying one -OH group to site-selective stannylation, even if the acetylene units are conjugated and hence, electronically coupled. An unusual temperature dependence was observed in that heating tends to improve site-selectivity, whereas per-stannylation is favored when the reaction is carried out in the cold. This counterintuitive trend can be rationalized based on spectroscopic data; additional support comes from the isolation of the unusual bimetallic complex 11. The bridging fulvene and enynyl ligands in 11 are thought to reflect an interligand redox isomerization process likely triggered by synchronous activation of the 1,3-diyne substrate by two metal centers. The preparative relevance of site-selective trans-hydrostannation is illustrated by the total synthesis of two members of the typhonoside series of glycolipids, which are endowed with neuroprotective properties. Moreover, the preparation of a fluoroalkene sphingosine analogue shows that the tin residue also serves as a versatile handle for late-stage modification of a bioactive target compound. Propargyl alcohols are privileged substrates for stereochemically unorthodox trans‐hydrostannation reactions catalyzed by [Cp*RuCl]4 (Cp*=pentamethylcyclopentadienyl), because an incipient hydrogen bond between the ‐OH group and the polarized [Ru‐Cl] unit assists substrate binding. For this very reason, it is also possible to subject diyne derivatives carrying one ‐OH group to site‐selective stannylation, even if the acetylene units are conjugated and hence, electronically coupled. An unusual temperature dependence was observed in that heating tends to improve site‐selectivity, whereas per‐stannylation is favored when the reaction is carried out in the cold. This counterintuitive trend can be rationalized based on spectroscopic data; additional support comes from the isolation of the unusual bimetallic complex 11. The bridging fulvene and enynyl ligands in 11 are thought to reflect an interligand redox isomerization process likely triggered by synchronous activation of the 1,3‐diyne substrate by two metal centers. The preparative relevance of site‐selective trans‐hydrostannation is illustrated by the total synthesis of two members of the typhonoside series of glycolipids, which are endowed with neuroprotective properties. Moreover, the preparation of a fluoroalkene sphingosine analogue shows that the tin residue also serves as a versatile handle for late‐stage modification of a bioactive target compound. |
| Author | Letort, Aurélien Roşca, Dragoş‐Adrian Mo, Xiaobin Higashida, Kosuke Fürstner, Alois |
| Author_xml | – sequence: 1 givenname: Xiaobin surname: Mo fullname: Mo, Xiaobin organization: Max-Planck-Institut für Kohlenforschung – sequence: 2 givenname: Aurélien surname: Letort fullname: Letort, Aurélien organization: Max-Planck-Institut für Kohlenforschung – sequence: 3 givenname: Dragoş‐Adrian surname: Roşca fullname: Roşca, Dragoş‐Adrian organization: Max-Planck-Institut für Kohlenforschung – sequence: 4 givenname: Kosuke surname: Higashida fullname: Higashida, Kosuke organization: Max-Planck-Institut für Kohlenforschung – sequence: 5 givenname: Alois orcidid: 0000-0003-0098-3417 surname: Fürstner fullname: Fürstner, Alois email: fuerstner@kofo.mpg.de organization: Max-Planck-Institut für Kohlenforschung |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29676822$$D View this record in MEDLINE/PubMed |
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| Copyright | 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. |
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| Keywords | natural products ruthenium glycolipids cooperativity organotin compounds trans-hydrometalation alkynes |
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| Snippet | Propargyl alcohols are privileged substrates for stereochemically unorthodox trans‐hydrostannation reactions catalyzed by [Cp*RuCl]4... Propargyl alcohols are privileged substrates for stereochemically unorthodox trans ‐hydrostannation reactions catalyzed by [Cp*RuCl] 4... Propargyl alcohols are privileged substrates for stereochemically unorthodox trans-hydrostannation reactions catalyzed by [Cp*RuCl]... Propargyl alcohols are privileged substrates for stereochemically unorthodox trans-hydrostannation reactions catalyzed by [Cp*RuCl]4... |
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| SubjectTerms | Acetylene Alcohols alkynes Bimetals Chemical reactions Chemistry cooperativity Data processing Fluorination Glycolipids Hydrogen bonds Isomerization natural products Neuroprotection organotin compounds ruthenium Substrates Synthesis Temperature dependence Tin trans-hydrometalation |
| Title | Site‐Selective trans‐Hydrostannation of 1,3‐ and 1,n‐Diynes: Application to the Total Synthesis of Typhonosides E and F, and a Fluorinated Cerebroside Analogue |
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