104066-58-2Relevant academic research and scientific papers
A Nazarov-Ene Tandem Reaction for the Stereoselective Construction of Spiro Compounds
Etling, Christoph,Tedesco, Giada,Kalesse, Markus
, p. 9257 - 9262 (2021)
The different reactivity of trienones under Lewis and Br?nsted acids catalysis was investigated, resulting in distinct cyclization products and carbon backbones that originated either from a conjugate Prins cyclization or an interrupted Nazarov cyclizatio
Collective Total Synthesis of Casbane Diterpenes: One Strategy, Multiple Targets
L?ffler, Lorenz E.,Wirtz, Conny,Fürstner, Alois
, p. 5316 - 5322 (2021/02/01)
Of the more than 100 casbane diterpenes known to date, only the eponymous parent hydrocarbon casbene itself has ever been targeted by chemical synthesis. Outlined herein is a conceptually new approach that brings not a single but a variety of casbane deri
Total synthesis of pinnatoxins A and G and revision of the mode of action of pinnatoxin A
Araoz, Romulo,Servent, Denis,Molgoi, Jordi,Iorga, Bogdan I.,Fruchart-Gaillard, Carole,Benoit, Evelyne,Gu, Zhenhua,Stivala, Craig,Zakarian, Armen
supporting information; experimental part, p. 10499 - 10511 (2011/09/14)
Pinnatoxins belong to an emerging class of potent marine toxins of the cyclic imine group. Detailed studies of their biological effects have been impeded by unavailability of the complex natural product from natural sources. This work describes the development of a robust, scalable synthetic sequence relying on a convergent strategy that delivered a sufficient amount of the toxin for detailed biological studies and its commercialization for use by other research groups and regulatory agencies. A central transformation in the synthesis is the highly diastereoselective Ireland-Claisen rearrangement of a complex α,α-disubstituted allylic ester based on a unique mode for stereoselective enolization through a chirality match between the substrate and the lithium amide base. With synthetic pinnatoxin A, a detailed study has been performed that provides conclusive evidence for its mode of action as a potent inhibitor of nicotinic acetylcholine receptors selective for the human neuronal α7 subtype. The comprehensive electrophysiological, biochemical, and computational studies support the view that the spiroimine subunit of pinnatoxins is critical for blocking nicotinic acetylcholine receptor subtypes, as evidenced by analyzing the effect of a synthetic analogue of pinnatoxin A containing an open form of the imine ring. Our studies have paved the way for the production of certified standards to be used for mass-spectrometric determination of these toxins in marine matrices and for the development of tests to detect these toxins in contaminated shellfish.
TRANSITION-METAL CATALYZED REGIOSELECTIVE ADDITION OF PhMe2SiBEt3Li AND Bu3SnBEt3Li TO ACETYLENIC COMPOUNDS IN THE PRESENCE OF METHANOL
Nozaki, Kyoko,Wakamatsu, Kuni,Nonaka, Tsuyoshi,Tueckmantel, Werner,Oshima, Koichiro,Utimoto, Kiitiro
, p. 2007 - 2010 (2007/10/02)
Treatment of acetylenic compounds with PhMe2SiBEt3Li in the presence of a transition-metal catalyst affords vinylsilanes in good yields.Coexistence of methanol as a proton source is essential for the completion of the reaction.
TRANSITION-METAL CATALYZED SILYLZINCATION AND SILYLALUMINATION OF ACETYLENIC COMPOUNDS
Wakamatsu, Kuni,Nonaka, Tsuyoshi,Okuda, Yasuhiro,Tueckmantel, Werner,Oshima, Koichiro,et al.
, p. 4427 - 4436 (2007/10/02)
Dialkyl(dimethylphenylsilyl)zinclithium and trialkyl(dimethylphenylsilyl)aluminiumlithium add effectively to internal acetylenes as well as terminal ones in the presence of transition-metal catalysts to provide vinylsilanes with high stereo- and regiosele
COPPER CATALYZED SILYLZINCATION OF ACETYLENES
Okuda, Yasuhiro,Wakamatsu, Kuni,Tueckmantel, Werner,Oshima, Koichiro,Nozaki, Hitosi
, p. 4629 - 4632 (2007/10/02)
Dialkyl(dimethylphenylsilyl)zinclithium adds effectively to internal acetylenes as well terminal acetylenes in the presence of CuCN catalyst.
