1283733-02-7Relevant academic research and scientific papers
A highly stereoselective and flexible strategy for the convergent synthesis of long-chain polydeoxypropionates: Application towards the synthesis of the glycolipid membrane components hydroxyphthioceranic and phthioceranic acid
Pischl, Matthias C.,Weise, Christian F.,Haseloff, Stefan,Müller, Marc-Andr,Pfaltz, Andreas,Schneider, Christoph
, p. 17360 - 17374 (2015/02/19)
A highly stereocontrolled and flexible access to biologically relevant polydeoxypropionates in optically pure form has been developed. Taking advantage of our previously established strategy for the asymmetric and stereo-divergent synthesis of trideoxypropionate building blocks, we have now been able to assemble large polydeoxypropio-nate chains with defined configuration in a highly convergent manner. Central steps of this approach include two Suzuki-Miyaura cross-coupling reactions with subsequent highly diastereoselective hydrogenations to join three advanced synthetic intermediates in excellent yield and with full stereochemical control. We have applied this strategy successfully towards the asymmetric synthesis of glycolipid membrane components phthioceranic acid and hydroxyphthioceranic acid, the latter of which was synthesized on a half-gram scale.
A general, asymmetric, and noniterative synthesis of trideoxypropionates. Straightforward syntheses of the pheromones (+)-vittatalactone and (+)-norvittatalactone
Weise, Christian F.,Pischl, Matthias C.,Pfaltz, Andreas,Schneider, Christoph
experimental part, p. 1477 - 1488 (2012/04/04)
A novel, highly stereocontrolled, and very flexible synthetic access to biologically relevant trideoxypropionate building blocks in optically pure form has been developed. On the basis of a three-step sequence comprising a thermal oxy-Cope rearrangement,
A non-iterative, flexible, and highly stereoselective synthesis of polydeoxypropionates-synthesis of (+)-vittatalactone
Weise, Christian F.,Pischl, Matthias,Pfaltz, Andreas,Schneider, Christoph
scheme or table, p. 3248 - 3250 (2011/05/05)
A short sequence comprising an oxy-Cope rearrangement, iridium-catalyzed hydrogenation, and enolate methylation provides trideoxypropionates with excellent diastereocontrol. A straightforward synthesis of the cucumber beetle pheromone (+)-vittatalactone i
