35042-52-5Relevant articles and documents
Stereoselective Total Synthesis of Atractylodemayne A, a Conjugated 2(E),8(Z),10(E)-Triene-4,6-diyne
Schmidt, Bernd,Aud?rsch, Stephan
, p. 1162 - 1165 (2016)
The first total synthesis of the polyacetylene natural product atractylodemayne A is reported. Stereoselective construction of the conjugated 8(Z),10(E)-diene moiety was achieved through a tethered ring-closing metathesis approach, comprising a Ru-catalyz
Stereoselective synthesis of the side chains of mycolactones A and B featuring stepwise double substitutions of 1,1-dibromo-1-alkenes
Yin, Ning,Wang, Guangwei,Qian, Mingxing,Negishi, Eiichi
, p. 2916 - 2920 (2006)
(Chemical Equation Presented) Piecing them together: The side chains of mycolactones A and B are synthesized with a high degree of stereoselectivity. The components of the side chains are prepared separately, then combined through Pd-catalyzed cross-coupling (see scheme; Z1 = tert- butyldimethylsilyl, Z2 = methoxymethyl, TBAF = tetra-n-butylammonium fluoride).
Search for highly efficient, stereoselective, and practical synthesis of complex organic compounds of medicinal importance as exemplified by the synthesis of the C21-C37 fragment of amphotericinb
Wang, Guangwei,Xu, Shiqing,Hu, Qian,Zeng, Fanxing,Negishi, Ei-Ichi
, p. 12938 - 12942 (2013)
Highly stereoselective: A highly efficient, stereoselective and practical synthesis of the C21-C37 fragment of amphotericinB was realized in 25 % overall yield in eight longest linear steps from commercially available ethyl (S)-3-hydroxybutyrate by using Fráter-Seebach alkylation, Brown crotylboration, Negishi coupling, Heck reaction, and Horner-Wadsworth-Emmons (HWE) olefination as key steps (see diagram). Copyright
On the Mechanism of Propynyloxirane Rearrangement
Abdullaev, T. Kh.,Fayzilov, I. U.,Isobaev, M. D.,Jumaeva, M. I.
, p. 1853 - 1860 (2021/12/22)
Abstract: The most probable mechanism for the opening of the oxirane ring in propynyloxirane (3-ethynyl-1,2-epoxypropane) is presented. Due to the rearrangement, a mixture of the Z and E isomers of enyne alcohols is formed. The 1H NMR data and quantum-chemical calculations revealed intramolecular interactions between the π-electrons of the triple bond and the OH proton in the six-membered ring of the Z isomer.
Chemo-, regio-, and stereoselective hydroboration of conjugated enyne alcohol/amine: Facile synthesis of Z,Z-/Z,E-1,3-dien-1/2-ylboronic ester bearing hydroxyl/amino group
Xu, Hua-Dong,Wu, Hao,Jiang, Chun,Chen, Peng,Shen, Mei-Hua
supporting information, p. 2915 - 2918 (2016/06/14)
Hydroboration of conjugated enyne alcohol/amine is studied by using copper salts and bis(pinacolato)diboron as pre-catalysts and boron source respectively. It is suggested that the chemo-selectivity is derived from a combined electronic influence of the heteroatoms on the substrate and the ligand on the transition metal. The regioselectivity is probably dominated mainly by electronic effect of the alkyne substituent. This study resulted in a highly selective protocol to access Z,Z-/Z,E-1,3-dien-1/2-ylboronic ester bearing hydroxyl/amino group.
