215876-09-8Relevant articles and documents
Enantioselective synthesis of oasomycin A, part II: Synthesis of the C29-C46 subunit
Evans, David A.,Nagorny, Pavel,Reynolds, Dominic J.,McRae, Kenneth J.
, p. 541 - 544 (2008/02/02)
(Chemical Equation Presented) Putting the pieces together: The total synthesis of the natural macrolide oasomycin A has been realized. Key fragment couplings include an anti-Felkin selective aldol addition (green), Kociensky-Julia olefinations (red), and
Diastereoselective synthesis of syn-3,5-dihydroxyesters via ruthenium-catalyzed asymmetric transfer hydrogenation
Everaere, Kathelyne,Franceschini, Nicolas,Mortreux, André,Carpentier, Jean-Fran?ois
, p. 2569 - 2571 (2007/10/03)
The asymmetric transfer hydrogenation of chiral 5-hydroxy-3-ketoesters in 2-propanol using chlororuthenium(II)arene/β-amino alcohol in situ catalyst combinations or a pre-synthesized Ru-{β-amino alcohol} true catalyst, provides syn-3,5-dihydroxyesters in
Application of complex aldol reactions to the total synthesis of phorboxazole B
Evans,Fitch,Smith,Cee
, p. 10033 - 10046 (2007/10/03)
The synthesis of phorboxazole B has been accomplished in 27 linear steps and an overall yield of 12.6%. The absolute stereochemistry of the C4-C12, C33-C38, and C13-C19 fragments was established utilizing catalytic asymmetric aldol methodology, while the absolute stereochemistry of the C20-C32 fragment was derived from an auxiliary-based asymmetric aldol reaction. All remaining chirality was incorporated through internal asymmetric induction, with the exception of the C43 stereocenter which was derived from (R)-trityl glycidol. Key fragment couplings include a stereoselective double stereodifferentiating aldol reaction, a metalated oxazole alkylation, an oxazole-stabilized Wittig olefination, and a chelation-controlled addition of the fully elaborated alkenyl metal side chain.
Asymmetric synthesis of bryostatin 2
Evans, David A.,Carter, Percy H.,Carreira, Erick M.,Prunet, Joelle A.,Charette, Andre B.,Lautens, Mark
, p. 2354 - 2359 (2007/10/03)
The potent bryostatin antitumor agents are currently in phase II clinical trials for the treatment of a variety of forms of cancer. Aldol reactions and directed reductions are among the essential steps for the formation of fragments A-C in the total synthesis of the title compound. Coupling of these fragments by sulfone-based olefination and alkylation reactions was followed by macrocyclization and introduction of the enoate moieties on rings B and C.