Stereoselective total synthesis of 4-((3S,5R)-3,5-dihydroxynonadecyl)phenol

Synthesis of Enantiomerically Pure Lignin Dimer Models for Catalytic Selectivity Studies

“…Intermediates 8a – 8c were then coupled with 4-hydroxy-3-methoxybenzaldehyde using specific Mitsunobu reaction conditions to yield protected ( S , S ) dimers 9a – 9c with complete inversion of configuration at the β-carbon. Under traditional Mitsunobu conditions in which the phosphine, secondary alcohol, and nucleophile were dissolved in organic solvent followed by the dropwise addition of azodicarboxylate, low yields were obtained (∼20%). , However, it was found that if the phosphine and azodicarboxylate were premixed to form the proposed zwitterionic species first, followed by the dropwise addition of 4-hydroxy-3-methoxybenzaldehyde (nucleophile) and intermediate 8 , a dramatic improvement in the yield (65%) could be realized. The TBS-ethers of compounds 9a – 9c were then deprotected using tetra- n -butylammonium fluoride (TBAF) to provide diols 10a – 10c .…”

Biologically bound nickel as a sustainable catalyst for the selective hydrogenation of cinnamaldehyde

“…[34], [47] HCAL and its derivatives have established themselves as industrially and biologically valuable in the synthesis of natural products, anti-viral pharmaceuticals, fragrances and chemosensors. [29], [28,50], [51] Our findings indicate that the presence of bio-carbon matrix around the naturally entrapped Ni enables an efficient suppression of the over-hydrogenation reaction pathway and carbonaceous accumulation on the surface. That is, the natural encapsulation of nickel on bio-carbon not only inhibits the unselective hydrogenation pathway but also regulates the electronic structure of Ni.…”

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

“…149) for synthesis of Hagens gland lactones [493]; (8) 1-octene with an amino acid derived acrylate ester [494], and with a homoallylic alcohol derivative [495]; (9) 1-decene with a vinyl-γ-lactone derivative for preparation of disparlures [496]; (10) 1-tridecene with a homoallylic alcohol derivative for preparation of a nonadecylphenol natural product [497], and with an allyl ether connected to a bis(carbohydrate) system (also employs 1-pentadecene or an allylglycerol derivative) [498]; (11) A c c e p t e d M a n u s c r i p t 28 antimalarial premarineosins [508]; (20) benzyl 13-tetradecenoate (158) and an alkene protected polyol derivative (e.g. 157) for total synthesis of penarolide sulfate A2 [509]; (21) a 1,5-diene ester derivative and an allylic alcohol derivative [510]; (22) styrene derivatives with a vinyltetrahydropyran for preparation of rhoiptelol B [511], with allylic diol for preparation of ginger diols [512], and with an alkene-phosphine oxide (e.g.…”