A base-mediated synthesis of < em > N < /em > -hydroxy- and < em > N < /em > -alkoxyindoles from 2-nitrostyrenes
Tetrahedron. 2023 Sep 7;144:133578. doi: 10.1016/j.tet.2023.133578. Epub 2023 Aug 6.ABSTRACTSequential treatment of alkyl 2-(2-nitroaryl)-2-butenoates with potassium tert-butoxide and an electrophile, such as methyl iodide, benzyl bromide and allyl bromide, afforded N-alkoxyindoles. In related reactions, using sodium tert-pentoxide as the base with or without in situ addition of an electrophile afforded N-alkoxy- and N-hydroxyindoles, respectively. Electrophiles such as dimethylsulfate, p-tosyl chloride, and acetic anhydride afforded moderate yields of the respective N-methoxy-, N-tosyloxy, and N-acetoxyindoles, while meth...
Source: Tetrahedron - September 8, 2023 Category: Chemistry Authors: Blaine T McClay Katharine E Lambson Serge R Banini Tural N Akhmedov Bj örn C G Söderberg Source Type: research
A base-mediated synthesis of < em > N < /em > -hydroxy- and < em > N < /em > -alkoxyindoles from 2-nitrostyrenes
Tetrahedron. 2023 Sep 7;144:133578. doi: 10.1016/j.tet.2023.133578. Epub 2023 Aug 6.ABSTRACTSequential treatment of alkyl 2-(2-nitroaryl)-2-butenoates with potassium tert-butoxide and an electrophile, such as methyl iodide, benzyl bromide and allyl bromide, afforded N-alkoxyindoles. In related reactions, using sodium tert-pentoxide as the base with or without in situ addition of an electrophile afforded N-alkoxy- and N-hydroxyindoles, respectively. Electrophiles such as dimethylsulfate, p-tosyl chloride, and acetic anhydride afforded moderate yields of the respective N-methoxy-, N-tosyloxy, and N-acetoxyindoles, while meth...
Source: Tetrahedron - September 8, 2023 Category: Chemistry Authors: Blaine T McClay Katharine E Lambson Serge R Banini Tural N Akhmedov Bj örn C G Söderberg Source Type: research
A base-mediated synthesis of < em > N < /em > -hydroxy- and < em > N < /em > -alkoxyindoles from 2-nitrostyrenes
Tetrahedron. 2023 Sep 7;144:133578. doi: 10.1016/j.tet.2023.133578. Epub 2023 Aug 6.ABSTRACTSequential treatment of alkyl 2-(2-nitroaryl)-2-butenoates with potassium tert-butoxide and an electrophile, such as methyl iodide, benzyl bromide and allyl bromide, afforded N-alkoxyindoles. In related reactions, using sodium tert-pentoxide as the base with or without in situ addition of an electrophile afforded N-alkoxy- and N-hydroxyindoles, respectively. Electrophiles such as dimethylsulfate, p-tosyl chloride, and acetic anhydride afforded moderate yields of the respective N-methoxy-, N-tosyloxy, and N-acetoxyindoles, while meth...
Source: Tetrahedron - September 8, 2023 Category: Chemistry Authors: Blaine T McClay Katharine E Lambson Serge R Banini Tural N Akhmedov Bj örn C G Söderberg Source Type: research
A base-mediated synthesis of < em > N < /em > -hydroxy- and < em > N < /em > -alkoxyindoles from 2-nitrostyrenes
Tetrahedron. 2023 Sep 7;144:133578. doi: 10.1016/j.tet.2023.133578. Epub 2023 Aug 6.ABSTRACTSequential treatment of alkyl 2-(2-nitroaryl)-2-butenoates with potassium tert-butoxide and an electrophile, such as methyl iodide, benzyl bromide and allyl bromide, afforded N-alkoxyindoles. In related reactions, using sodium tert-pentoxide as the base with or without in situ addition of an electrophile afforded N-alkoxy- and N-hydroxyindoles, respectively. Electrophiles such as dimethylsulfate, p-tosyl chloride, and acetic anhydride afforded moderate yields of the respective N-methoxy-, N-tosyloxy, and N-acetoxyindoles, while meth...
Source: Tetrahedron - September 8, 2023 Category: Chemistry Authors: Blaine T McClay Katharine E Lambson Serge R Banini Tural N Akhmedov Bj örn C G Söderberg Source Type: research
A base-mediated synthesis of < em > N < /em > -hydroxy- and < em > N < /em > -alkoxyindoles from 2-nitrostyrenes
Tetrahedron. 2023 Sep 7;144:133578. doi: 10.1016/j.tet.2023.133578. Epub 2023 Aug 6.ABSTRACTSequential treatment of alkyl 2-(2-nitroaryl)-2-butenoates with potassium tert-butoxide and an electrophile, such as methyl iodide, benzyl bromide and allyl bromide, afforded N-alkoxyindoles. In related reactions, using sodium tert-pentoxide as the base with or without in situ addition of an electrophile afforded N-alkoxy- and N-hydroxyindoles, respectively. Electrophiles such as dimethylsulfate, p-tosyl chloride, and acetic anhydride afforded moderate yields of the respective N-methoxy-, N-tosyloxy, and N-acetoxyindoles, while meth...
Source: Tetrahedron - September 8, 2023 Category: Chemistry Authors: Blaine T McClay Katharine E Lambson Serge R Banini Tural N Akhmedov Bj örn C G Söderberg Source Type: research
A base-mediated synthesis of < em > N < /em > -hydroxy- and < em > N < /em > -alkoxyindoles from 2-nitrostyrenes
Tetrahedron. 2023 Sep 7;144:133578. doi: 10.1016/j.tet.2023.133578. Epub 2023 Aug 6.ABSTRACTSequential treatment of alkyl 2-(2-nitroaryl)-2-butenoates with potassium tert-butoxide and an electrophile, such as methyl iodide, benzyl bromide and allyl bromide, afforded N-alkoxyindoles. In related reactions, using sodium tert-pentoxide as the base with or without in situ addition of an electrophile afforded N-alkoxy- and N-hydroxyindoles, respectively. Electrophiles such as dimethylsulfate, p-tosyl chloride, and acetic anhydride afforded moderate yields of the respective N-methoxy-, N-tosyloxy, and N-acetoxyindoles, while meth...
Source: Tetrahedron - September 8, 2023 Category: Chemistry Authors: Blaine T McClay Katharine E Lambson Serge R Banini Tural N Akhmedov Bj örn C G Söderberg Source Type: research
A base-mediated synthesis of < em > N < /em > -hydroxy- and < em > N < /em > -alkoxyindoles from 2-nitrostyrenes
Tetrahedron. 2023 Sep 7;144:133578. doi: 10.1016/j.tet.2023.133578. Epub 2023 Aug 6.ABSTRACTSequential treatment of alkyl 2-(2-nitroaryl)-2-butenoates with potassium tert-butoxide and an electrophile, such as methyl iodide, benzyl bromide and allyl bromide, afforded N-alkoxyindoles. In related reactions, using sodium tert-pentoxide as the base with or without in situ addition of an electrophile afforded N-alkoxy- and N-hydroxyindoles, respectively. Electrophiles such as dimethylsulfate, p-tosyl chloride, and acetic anhydride afforded moderate yields of the respective N-methoxy-, N-tosyloxy, and N-acetoxyindoles, while meth...
Source: Tetrahedron - September 8, 2023 Category: Chemistry Authors: Blaine T McClay Katharine E Lambson Serge R Banini Tural N Akhmedov Bj örn C G Söderberg Source Type: research
A symmetry-driven approach toward the total synthesis of dodecahedrane
Tetrahedron. 2022 Nov 5;126:133041. doi: 10.1016/j.tet.2022.133041. Epub 2022 Sep 21.ABSTRACTHerein, we describe our progress toward the total synthesis of dodecahedrane, a complex and highly symmetrical hydrocarbon that bears twelve fused rings arranged in a cage-like architecture. Central to our approach is a late-stage [2+2+2+2+2] polyene cyclization cascade, which is expected to construct five new bonds and ten new rings in a single transformation. Toward this end, we describe efforts to synthesize key monomeric fragments, along with successful dimerization studies using a pinacol coupling approach. Subsequent studies ...
Source: Tetrahedron - September 4, 2023 Category: Chemistry Authors: Jason V Chari Luca McDermott Jacob E Dander Bryan J Simmons Neil K Garg Source Type: research
A symmetry-driven approach toward the total synthesis of dodecahedrane
Tetrahedron. 2022 Nov 5;126:133041. doi: 10.1016/j.tet.2022.133041. Epub 2022 Sep 21.ABSTRACTHerein, we describe our progress toward the total synthesis of dodecahedrane, a complex and highly symmetrical hydrocarbon that bears twelve fused rings arranged in a cage-like architecture. Central to our approach is a late-stage [2+2+2+2+2] polyene cyclization cascade, which is expected to construct five new bonds and ten new rings in a single transformation. Toward this end, we describe efforts to synthesize key monomeric fragments, along with successful dimerization studies using a pinacol coupling approach. Subsequent studies ...
Source: Tetrahedron - September 4, 2023 Category: Chemistry Authors: Jason V Chari Luca McDermott Jacob E Dander Bryan J Simmons Neil K Garg Source Type: research
A symmetry-driven approach toward the total synthesis of dodecahedrane
Tetrahedron. 2022 Nov 5;126:133041. doi: 10.1016/j.tet.2022.133041. Epub 2022 Sep 21.ABSTRACTHerein, we describe our progress toward the total synthesis of dodecahedrane, a complex and highly symmetrical hydrocarbon that bears twelve fused rings arranged in a cage-like architecture. Central to our approach is a late-stage [2+2+2+2+2] polyene cyclization cascade, which is expected to construct five new bonds and ten new rings in a single transformation. Toward this end, we describe efforts to synthesize key monomeric fragments, along with successful dimerization studies using a pinacol coupling approach. Subsequent studies ...
Source: Tetrahedron - September 4, 2023 Category: Chemistry Authors: Jason V Chari Luca McDermott Jacob E Dander Bryan J Simmons Neil K Garg Source Type: research
A symmetry-driven approach toward the total synthesis of dodecahedrane
Tetrahedron. 2022 Nov 5;126:133041. doi: 10.1016/j.tet.2022.133041. Epub 2022 Sep 21.ABSTRACTHerein, we describe our progress toward the total synthesis of dodecahedrane, a complex and highly symmetrical hydrocarbon that bears twelve fused rings arranged in a cage-like architecture. Central to our approach is a late-stage [2+2+2+2+2] polyene cyclization cascade, which is expected to construct five new bonds and ten new rings in a single transformation. Toward this end, we describe efforts to synthesize key monomeric fragments, along with successful dimerization studies using a pinacol coupling approach. Subsequent studies ...
Source: Tetrahedron - September 4, 2023 Category: Chemistry Authors: Jason V Chari Luca McDermott Jacob E Dander Bryan J Simmons Neil K Garg Source Type: research
Progress Toward the Asymmetric de Novo Synthesis of Lanostanes: A Counter Biomimetic Cucurbitane-to-Lanostane Type Transformation
Tetrahedron. 2023 Jul 17;141:133498. doi: 10.1016/j.tet.2023.133498. Epub 2023 Jun 2.ABSTRACTAn oxidative rearrangement has been established that enables a cucurbitane-to-lanostane type rearrangement that is counter to known biomimetic transformations that proceed in an opposite direction by way of a lanostane-to-cucurbitane transformation. Here, an oxidative dearomatization/Wagner-Meerwein rearrangement with a substrate bearing the characteristic cucurbitane triad of quaternary centers at C9, C13 and C14, and possessing an alkene at C11-C12, proceeds in a manner that selectively shifts the methyl group at C9 to C10 in con...
Source: Tetrahedron - August 28, 2023 Category: Chemistry Authors: Andrea R Bucknam Glenn C Micalizio Source Type: research
Progress Toward the Asymmetric de Novo Synthesis of Lanostanes: A Counter Biomimetic Cucurbitane-to-Lanostane Type Transformation
Tetrahedron. 2023 Jul 17;141:133498. doi: 10.1016/j.tet.2023.133498. Epub 2023 Jun 2.ABSTRACTAn oxidative rearrangement has been established that enables a cucurbitane-to-lanostane type rearrangement that is counter to known biomimetic transformations that proceed in an opposite direction by way of a lanostane-to-cucurbitane transformation. Here, an oxidative dearomatization/Wagner-Meerwein rearrangement with a substrate bearing the characteristic cucurbitane triad of quaternary centers at C9, C13 and C14, and possessing an alkene at C11-C12, proceeds in a manner that selectively shifts the methyl group at C9 to C10 in con...
Source: Tetrahedron - August 28, 2023 Category: Chemistry Authors: Andrea R Bucknam Glenn C Micalizio Source Type: research
Progress Toward the Asymmetric de Novo Synthesis of Lanostanes: A Counter Biomimetic Cucurbitane-to-Lanostane Type Transformation
Tetrahedron. 2023 Jul 17;141:133498. doi: 10.1016/j.tet.2023.133498. Epub 2023 Jun 2.ABSTRACTAn oxidative rearrangement has been established that enables a cucurbitane-to-lanostane type rearrangement that is counter to known biomimetic transformations that proceed in an opposite direction by way of a lanostane-to-cucurbitane transformation. Here, an oxidative dearomatization/Wagner-Meerwein rearrangement with a substrate bearing the characteristic cucurbitane triad of quaternary centers at C9, C13 and C14, and possessing an alkene at C11-C12, proceeds in a manner that selectively shifts the methyl group at C9 to C10 in con...
Source: Tetrahedron - August 28, 2023 Category: Chemistry Authors: Andrea R Bucknam Glenn C Micalizio Source Type: research
Progress Toward the Asymmetric de Novo Synthesis of Lanostanes: A Counter Biomimetic Cucurbitane-to-Lanostane Type Transformation
Tetrahedron. 2023 Jul 17;141:133498. doi: 10.1016/j.tet.2023.133498. Epub 2023 Jun 2.ABSTRACTAn oxidative rearrangement has been established that enables a cucurbitane-to-lanostane type rearrangement that is counter to known biomimetic transformations that proceed in an opposite direction by way of a lanostane-to-cucurbitane transformation. Here, an oxidative dearomatization/Wagner-Meerwein rearrangement with a substrate bearing the characteristic cucurbitane triad of quaternary centers at C9, C13 and C14, and possessing an alkene at C11-C12, proceeds in a manner that selectively shifts the methyl group at C9 to C10 in con...
Source: Tetrahedron - August 28, 2023 Category: Chemistry Authors: Andrea R Bucknam Glenn C Micalizio Source Type: research
