754201-28-0Relevant academic research and scientific papers
Nickel-Catalyzed Enantioselective Conjunctive Cross-Coupling of 9-BBN Borates
Chierchia, Matteo,Law, Chunyin,Morken, James P.
, p. 11870 - 11874 (2017)
Catalytic enantioselective conjunctive cross-coupling between 9-BBN borate complexes and aryl electrophiles can be accomplished with Ni salts in the presence of a chiral diamine ligand. The reactions furnish chiral 9-BBN derivatives in an enantioselective fashion and these are converted to chiral alcohols and amines, or engaged in other stereospecific C?C bond forming reactions.
Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope
Yan, Lu,Meng, Yan,Haeffner, Fredrik,Leon, Robert M.,Crockett, Michael P.,Morken, James P.
supporting information, p. 3663 - 3673 (2018/03/21)
A mechanistic investigation of the carbohydrate/DBU cocatalyzed enantioselective diboration of alkenes is presented. These studies provide an understanding of the origin of stereoselectivity and also reveal a strategy for enhancing reactivity and broadening the substrate scope.
Synthesis of (3R,5S)-5-hydroxy-de-O-methyllasiodiplodin: A facile and stereoselective approach
Bujaranipalli, Sheshurao,Das, Saibal
supporting information, p. 3747 - 3749 (2015/06/08)
A concise and facile synthesis of (3R,5S)-5-hydroxy-de-O-methyllasiodiplodin has been demonstrated in 12 steps starting from methylacetoacetate and (±)propylene oxide. The key reactions involved are Jacobsen's hydrolytic kinetic resolution, Sharpless asymmetric epoxidation, Mitsunobu, and ring closing metathesis reaction for the construction of macrolactone with two chiral substitutions on it.
Towards the total synthesis of marineosin A: Construction of the macrocyclic pyrrole and an advanced, functionalized spiroaminal model
Aldrich, Leslie N.,Berry, Cynthia B.,Bates, Brittney S.,Konkol, Leah C.,So, Miranda,Lindsley, Craig W.
supporting information, p. 4215 - 4218 (2013/07/26)
Herein, we describe the enantioselective construction of the 12-membered macrocyclic pyrrole core of marineosin A in 5.1 % overall yield from (S)-propylene oxide. The route features a key Stetter reaction to install a 1,4-diketone, which is subjected to Paal-Knorr pyrrole synthesis and ring-closing metathesis to afford the macrocycle. A divergence point in the synthetic scheme also enabled access to a highly functionalized spiroaminal model system through an acid-mediated hydroxy oxo amide cyclization strategy. Copyright
Modular asymmetric synthesis of pochonin C
Barluenga, Sofia,Lopez, Pilar,Moulin, Emilie,Winssinger, Nicolas
, p. 3467 - 3470 (2007/10/03)
Back to its origins: Pochonin C was synthesized in 11 steps from the four fragments shown in the scheme. This asymmetric synthesis and the conversion of pochonin C into radicicol defines the configuration at the center bearing the chlorine atom as S. lpc
A practical, stereospecific route to 18-, 19-, and 20-hydroxyeicosa-5(Z), 8(Z),11(Z),14(Z)-tetraenoic acids (18-, 19-, and 20-HETEs)
Gopal, V. Raj,Jagadeesh,Reddy, Y. Krishna,Bandyopadhyay,Capdevila, Jorge H.,Falck
, p. 2563 - 2565 (2007/10/03)
Suzuki-Miyaura cross-coupling of cis-vinylbromide 6, obtained in three steps from diol 4, with functionalized boranes provides a practical, stereospecific route to the title CYP P450 eicosanoids.
