133210-25-0Relevant academic research and scientific papers
Pd-catalyzed cross-coupling of terminal alkynes with ene-yne-ketones: Access to conjugated enynes via metal carbene migratory insertion
Xia, Ying,Liu, Zhen,Ge, Rui,Xiao, Qing,Zhang, Yan,Wang, Jianbo
, p. 11233 - 11235 (2015)
A novel strategy for alkyne-alkyne cross-coupling has been developed under the palladium catalysis. In this reaction, ene-yne-ketones are employed as carbene precursors, which couple with terminal alkynes through the metal carbene migratory insertion process. Furan-substituted enynes are obtained in good yields and in a stereoselective manner.
Enantioselective Intramolecular C?H Insertion of Donor and Donor/Donor Carbenes by a Nondiazo Approach
Zhu, Dong,Ma, Jun,Luo, Kui,Fu, Hongguang,Zhang, Li,Zhu, Shifa
, p. 8452 - 8456 (2016/07/19)
The first enantioselective intramolecular C?H insertion and cyclopropanation reactions of donor- and donor/donor-carbenes by a nondiazo approach are reported. The reactions were conducted in a one-pot manner without slow addition and provided the desired
Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (-)-isocyclocapitelline, and (-)-isochrysotricine
Volz, Frank,Wadman, Sipke H.,Hoffmann-R?der, Anja,Krause, Norbert
experimental part, p. 1902 - 1910 (2009/06/20)
A stereoselective synthesis of the tetrahydrofuran-containing natural products (2S,5R)-(+)-linalool oxide (1), (-)-isocyclocapitelline (2), and (-)-isochrysotricine (3) is reported. Key steps are the copper-mediated SN2′-substitution of proparg
Golden opportunities in natural product synthesis: First total synthesis of (-)-isocyclocapitelline and (-)-isochrysotricine by gold-catalyzed allene cycloisomerization
Volz, Frank,Krause, Norbert
, p. 1519 - 1521 (2008/02/05)
The first enantioselective total syntheses of the β-carboline alkaloids (-)-isochrysotricine (1) and (-)-isocyclocapitelline (2) are reported which confirm the absolute configuration of these natural products. Key steps are the copper-mediated SN/su
Primary and secondary allyltitanium(IV) reagents in aldehyde allylation II: Application to an enantioselective preparation of a C1-C7 fragment of spiramycin
Razon, Patrick,N'Zoutani, Marie-Ange,Dhulut, Sylvie,Bezzenine-Lafollee, Sophie,Pancrazi, Ange,Ardisson, Janick
, p. 109 - 121 (2007/10/03)
A synthetic approach to the eastern part of spiramycin, an important antibiotic compound, is described. Introduction of the side chain was first envisaged through a Hoppe aldehyde allylation. This reaction was carried out between an optically pure aldehyde 32 and a (±)-γ-alkoxy allyltitanium(IV) species derived from a primary γ-alkoxy allyl (diisopropyl)carbamate. Under kinetic resolution conditions, the anti-Cram compound 35 was obtained in an 80:20 mixture, with the Cram isomer 34, in 81% yield. Employing the optically pure (S)-γ-alkoxy allyl (diisopropyl)carbamate 36, the corresponding (R)-γ-alkoxy allyltitanium (R)-'Ti'-III was generated under n-BuLi·TMEDA/Ti(Oi-Pr)4 conditions, that reacted with aldehyde 32 in double stereodifferentiation to deliver the expected Cram compound 40 in 80% yield (95% de). This latter corresponded to the C1-C7 fragment of spiramycin.
