84695-29-4Relevant articles and documents
Single-electron/pericyclic cascade for the synthesis of dienes
Campbell, Natalie E.,Sammis, Glenn M.
supporting information, p. 6228 - 6231 (2014/06/23)
The highly efficient and diastereoselective synthesis of E dienes has been accomplished through radical cyclization of bromoallyl hydrazones. This methodology has been further extended to generate these products through a one-pot condensation/radical cyclization/cycloreversion cascade from simple aldehyde starting materials in high yields (>75 %) and high diastereoselectivities (>95:5). Mechanistic investigations suggest that the cascade reaction proceeds through a cyclic diazene intermediate prior to the cycloreversion.
Synthesis of the conjugated tetraene acid side chain of mycolactone e by Suzuki-Miyaura cross-coupling reaction of alkenyl boronates
Wang, Yuan,Dai, Wei-Min
supporting information, p. 323 - 330 (2014/01/23)
The conjugated tetraene acid side chain of mycolactone E has been synthesized by the cross-coupling reaction of a trisubstituted triene bromide with a trisubstituted alkenyl boronate catalyzed by Pd(OAc)2-Aphos-Y under mildly basic conditions [K3PO4·3H 2O, H2O, tetrahydrofuran (THF), 35 °C, 18 h]. The conjugated tetraene product was obtained in 85 % yield without geometrical isomer(s) under the catalytic conditions. These results demonstrated that the coupling of alkenyl halides with alkenyl boronates catalyzed by Pd(OAc) 2-Aphos-Y in combination with CuI-catalyzed regio- and stereoselective alkyne borylation offers an efficient synthetic tool for accessing conjugated polyene molecules. Gently united: Conjugate polyenes possessing trisubstituted double bond(s) are synthesized from trisubstituted alkenyl halides and trisubstituted boronates in high yields under the catalysis of the hemilabile P,O ligand Aphos-Y and Pd(OAc)2 in the presence of K3PO4·3H2O (3 equiv.) and H2O (18 equiv.) in tetrahydrofuran (THF) at 35°C. The product is free of geometric isomers. Copyright
Studies on the synthesis of apoptolidin A. 1. Synthesis of the C(1)-C(11) fragment
Handa, Masaki,Scheldt, Karl A.,Bossart, Martin,Zheng, Nan,Roush, William R.
, p. 1031 - 1035 (2008/09/18)
(Chemical Equation Presented) A synthesis of the C(1)-C(11) fragment of apoptolidin A has been accomplished by a convergent route involving the stereoselective glycosidation of 9 and the Suzuki cross-coupling reaction of bromodienoate 7 and the vinylboran