The Experts below are selected from a list of 240 Experts worldwide ranked by ideXlab platform
Rodrigo B Andrade - One of the best experts on this subject based on the ideXlab platform.
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Total Synthesis of Strychnos Alkaloids Akuammicine, Strychnine, and Leuconicines A and B
Strategies and Tactics in Organic Synthesis, 2013Co-Authors: Gopal Sirasani, Rodrigo B AndradeAbstract:Abstract Described herein is an account of my laboratory’s entry into the magnificent field of complex alkaloid total synthesis, spanning the development of novel methods for quickly assembling polycyclic frameworks through the total synthesis of various members of the Strychnos alkaloids. A discussion of the prior art related to our approach to these alkaloids in addition to strategic decisions and reasoning made en route to targets Akuammicine ( 1 ), strychnine ( 2 ), and leuconicines A ( 3 ) and B ( 4 ) is carefully detailed. Finally, we present the retrosynthetic analyses of the aforementioned targets and respective total syntheses thereof (including asymmetric variants).
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Concise Total Synthesis of (.+-.)-Strychnine and (.+-.)-Akuammicine.
ChemInform, 2010Co-Authors: Gopal Sirasani, Tapas Paul, Scott Kassel, William Jr. Dougherty, Rodrigo B AndradeAbstract:The formation of the title compounds is achieved via previously reported sequential one-pot spirocyclization/intramolecular aza-Baylis—Hillman procedure.
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concise total synthesis of strychnine and Akuammicine
ChemInform, 2010Co-Authors: Gopal Sirasani, Tapas Paul, Scott Kassel, William Jr. Dougherty, Rodrigo B AndradeAbstract:The formation of the title compounds is achieved via previously reported sequential one-pot spirocyclization/intramolecular aza-Baylis—Hillman procedure.
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Concise Total Syntheses of (±)-Strychnine and (±)-Akuammicine†
The Journal of organic chemistry, 2010Co-Authors: Gopal Sirasani, Tapas Paul, William G Dougherty, Scott Kassel, Rodrigo B AndradeAbstract:Concise total syntheses of Strychnos alkaloids strychnine (1) and Akuammicine (2) have been realized in 13 and 6 operations, respectively. Key steps include (1) the vinylogous Mannich reaction; (2) a novel, sequential one-pot spirocyclization/intramolecular aza-Baylis−Hillman reaction; and (3) a Heck cyclization. The synthesis of 1 proceeds via the Wieland−Gumlich aldehyde (26).
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concise total syntheses of strychnine and Akuammicine
Journal of Organic Chemistry, 2010Co-Authors: Gopal Sirasani, Tapas Paul, William G Dougherty, Scott Kassel, Rodrigo B AndradeAbstract:Concise total syntheses of Strychnos alkaloids strychnine (1) and Akuammicine (2) have been realized in 13 and 6 operations, respectively. Key steps include (1) the vinylogous Mannich reaction; (2) a novel, sequential one-pot spirocyclization/intramolecular aza-Baylis−Hillman reaction; and (3) a Heck cyclization. The synthesis of 1 proceeds via the Wieland−Gumlich aldehyde (26).
G. Hugel - One of the best experts on this subject based on the ideXlab platform.
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The flow thermolysis of pseudoakuammigine
Tetrahedron Letters, 1997Co-Authors: G. Hugel, J. LevyAbstract:Abstract Flow-thermolysis of pseudo-akuammigine ( 5 ) yielded 15,16- seco -14,15-dehydropseudo-akuammigine ( 6 ) with a cis C/D ring junction.
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Flow Thermolysis Rearrangements in the Indole Alkaloid Series: Strictamine and Akuammicine Derivatives. The Absolute Configurations of Ngouniensine and epi-Ngouniensine.
The Journal of organic chemistry, 1997Co-Authors: G. Hugel, Louisette Le Men-olivier, Daniel Royer, Bernard Richard, Marie-josé Jacquier, Jean LévyAbstract:Flow thermolysis of strictamine (1) generated two of the predictable rearrangement products, resulting from [1,5]-sigmatropic shifts: Akuammicine (2) and indolenine 9. Besides formation of these two compounds, a quite different pathway gave rise to a novel rearrangement leading to indole 6, with the framework of the natural alkaloid ngouniensine (19). Rearrangement to the ngouniensine skeleton became the major pathway when the Akuammicine derivatives 10, 12, and 17 were submitted to thermolysis, generating compounds 11, 13 + 15, and 18, respectively. These results allowed us to assign the absolute configuration of (−)-ngouniensine (19) (3R,20R) and that of (−)-epingouniensine ((−)-21) (3R,20S).
Gopal Sirasani - One of the best experts on this subject based on the ideXlab platform.
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Total Synthesis of Strychnos Alkaloids Akuammicine, Strychnine, and Leuconicines A and B
Strategies and Tactics in Organic Synthesis, 2013Co-Authors: Gopal Sirasani, Rodrigo B AndradeAbstract:Abstract Described herein is an account of my laboratory’s entry into the magnificent field of complex alkaloid total synthesis, spanning the development of novel methods for quickly assembling polycyclic frameworks through the total synthesis of various members of the Strychnos alkaloids. A discussion of the prior art related to our approach to these alkaloids in addition to strategic decisions and reasoning made en route to targets Akuammicine ( 1 ), strychnine ( 2 ), and leuconicines A ( 3 ) and B ( 4 ) is carefully detailed. Finally, we present the retrosynthetic analyses of the aforementioned targets and respective total syntheses thereof (including asymmetric variants).
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Concise Total Synthesis of (.+-.)-Strychnine and (.+-.)-Akuammicine.
ChemInform, 2010Co-Authors: Gopal Sirasani, Tapas Paul, Scott Kassel, William Jr. Dougherty, Rodrigo B AndradeAbstract:The formation of the title compounds is achieved via previously reported sequential one-pot spirocyclization/intramolecular aza-Baylis—Hillman procedure.
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concise total synthesis of strychnine and Akuammicine
ChemInform, 2010Co-Authors: Gopal Sirasani, Tapas Paul, Scott Kassel, William Jr. Dougherty, Rodrigo B AndradeAbstract:The formation of the title compounds is achieved via previously reported sequential one-pot spirocyclization/intramolecular aza-Baylis—Hillman procedure.
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Concise Total Syntheses of (±)-Strychnine and (±)-Akuammicine†
The Journal of organic chemistry, 2010Co-Authors: Gopal Sirasani, Tapas Paul, William G Dougherty, Scott Kassel, Rodrigo B AndradeAbstract:Concise total syntheses of Strychnos alkaloids strychnine (1) and Akuammicine (2) have been realized in 13 and 6 operations, respectively. Key steps include (1) the vinylogous Mannich reaction; (2) a novel, sequential one-pot spirocyclization/intramolecular aza-Baylis−Hillman reaction; and (3) a Heck cyclization. The synthesis of 1 proceeds via the Wieland−Gumlich aldehyde (26).
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concise total syntheses of strychnine and Akuammicine
Journal of Organic Chemistry, 2010Co-Authors: Gopal Sirasani, Tapas Paul, William G Dougherty, Scott Kassel, Rodrigo B AndradeAbstract:Concise total syntheses of Strychnos alkaloids strychnine (1) and Akuammicine (2) have been realized in 13 and 6 operations, respectively. Key steps include (1) the vinylogous Mannich reaction; (2) a novel, sequential one-pot spirocyclization/intramolecular aza-Baylis−Hillman reaction; and (3) a Heck cyclization. The synthesis of 1 proceeds via the Wieland−Gumlich aldehyde (26).
Yong Tang - One of the best experts on this subject based on the ideXlab platform.
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reaction of donor acceptor cyclobutanes with indoles a general protocol for the formal total synthesis of strychnine and the total synthesis of Akuammicine
Angewandte Chemie, 2017Co-Authors: Liangwen Feng, Hai Ren, Hu Xiong, Pan Wang, Lijia Wang, Yong TangAbstract:A ligand-promoted catalytic [4+2] annulation reaction using indole derivatives and donor-acceptor (D-A) cyclobutanes is reported, thus providing an efficient and atom-economical access to versatile cyclohexa-fused indolines with excellent levels of diastereoselectivity and a broad substrate scope. In the presence of a chiral SaBOX ligand, excellent enantioselectivity was realized with up to 94 % ee. This novel synthetic method is applied as a general protocol for the total synthesis of (±)-Akuammicine and the formal total synthesis of (±)-strychnine from the same common-core scaffold.
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Reaction of Donor‐Acceptor Cyclobutanes with Indoles: A General Protocol for the Formal Total Synthesis of (±)‐Strychnine and the Total Synthesis of (±)‐Akuammicine
Angewandte Chemie (International ed. in English), 2017Co-Authors: Liangwen Feng, Hai Ren, Hu Xiong, Pan Wang, Lijia Wang, Yong TangAbstract:A ligand-promoted catalytic [4+2] annulation reaction using indole derivatives and donor-acceptor (D-A) cyclobutanes is reported, thus providing an efficient and atom-economical access to versatile cyclohexa-fused indolines with excellent levels of diastereoselectivity and a broad substrate scope. In the presence of a chiral SaBOX ligand, excellent enantioselectivity was realized with up to 94 % ee. This novel synthetic method is applied as a general protocol for the total synthesis of (±)-Akuammicine and the formal total synthesis of (±)-strychnine from the same common-core scaffold.
Jean Lévy - One of the best experts on this subject based on the ideXlab platform.
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Flow Thermolysis Rearrangements in the Indole Alkaloid Series: Strictamine and Akuammicine Derivatives. The Absolute Configurations of Ngouniensine and epi-Ngouniensine.
The Journal of organic chemistry, 1997Co-Authors: G. Hugel, Louisette Le Men-olivier, Daniel Royer, Bernard Richard, Marie-josé Jacquier, Jean LévyAbstract:Flow thermolysis of strictamine (1) generated two of the predictable rearrangement products, resulting from [1,5]-sigmatropic shifts: Akuammicine (2) and indolenine 9. Besides formation of these two compounds, a quite different pathway gave rise to a novel rearrangement leading to indole 6, with the framework of the natural alkaloid ngouniensine (19). Rearrangement to the ngouniensine skeleton became the major pathway when the Akuammicine derivatives 10, 12, and 17 were submitted to thermolysis, generating compounds 11, 13 + 15, and 18, respectively. These results allowed us to assign the absolute configuration of (−)-ngouniensine (19) (3R,20R) and that of (−)-epingouniensine ((−)-21) (3R,20S).
