343221-33-0Relevant academic research and scientific papers
Tandem oxidation-dehydrogenation of (hetero)arylated primary alcohols via perruthenate catalysis
Bettencourt, Christian J.,Chow, Sharon,Moore, Peter W.,Read, Christopher D.G.,Jiao, Yanxiao,Bakker, Jan Peter,Zhao, Sheng,Bernhardt, Paul V.,Williams, Craig M.
, p. 652 - 659 (2021/09/08)
Tandem oxidative-dehydrogenation of primary alcohols to give a,b-unsaturated aldehydes in one pot are rare transformations in organic synthesis, with only two methods currently available. Reported herein is a novel method using the bench-stable salt methyltriphenylphosphonium perruthenate (MTP3), and a new co-oxidant NEMO&middoPF6 (NEMO = N-ethyl-N-hydroxymorpholinium) which provides unsaturated aldehydes in low to moderate yields. The Ley-Griffith oxidation of (hetero)arylated primary alcohols with N-oxide co-oxidants NMO (NMO = N-methylmorpholine N-oxide)/NEMO, is expanded by addition of the N-oxide salt NEMO&middoPF6 to convert the intermediate saturated aldehyde into its unsaturated counterpart. The discovery, method development, reaction scope, and associated challenges of this method are highlighted. The conceptual value of late-stage dehydrogenation in natural product synthesis is demonstrated via the synthesis of a polyene scaffold related to auxarconjugatin B.
Evolution of a protecting-group-free total synthesis: Studies en route to the neuroactive marine macrolide (-)-palmyrolide A
Tello-Aburto, Rodolfo,Newar, Tara D.,Maio, William A.
experimental part, p. 6271 - 6289 (2012/09/22)
A full account of our synthetic work toward the first total synthesis of the neuroactive marine macrolide (-)-palmyrolide A is described. Our first-generation approach aimed to unlock the unknown C(5)-C(7) stereochemical relationship via the synthesis of
Liposomal formulation of retinoids designed for enzyme triggered release
Pedersen, Palle J.,Adolph, Sidsel K.,Subramanian, Arun K.,Arouri, Ahmad,Andresen, Thomas L.,Mouritsen, Ole G.,Madsen, Robert,Madsen, Mogens W.,Peters, Günther H.,Clausen, Mads H.
supporting information; experimental part, p. 3782 - 3792 (2010/08/06)
The design of retinoid phospholipid prodrugs is described based on molecular dynamics simulations and cytotoxicity studies of synthetic retinoid esters. The prodrugs are degradable by secretory phospholipase A2 IIA and have potential in liposomal drug delivery targeting tumors. We have synthesized four different retinoid phospholipid prodrugs and shown that they form particles in the liposome size region with average diameters of 94-118 nm. Upon subjection to phospholipase A2, the lipid prodrugs were hydrolyzed, releasing cytotoxic retinoids and lysolipids. The formulated lipid prodrugs displayed IC50 values in the range of 3-19 μM toward HT-29 and Colo205 colon cancer cells in the presence of phospholipase A 2, while no significant cell death was observed in the absence of the enzyme.
Total synthesis of (+)-crocacin D
Dias, Luiz C.,De Oliveira, Luciana G.,Vilcachagua, Janaina D.,Nigsch, Florian
, p. 2225 - 2234 (2007/10/03)
(Chemical Equation Presented) The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moie
