The synthesis and configurational stability of differentially protected .beta.-hydroxy-.alpha.-amino aldehydes

Abstract

Methyl 2-Cyano-5-(hydroxymethyl)-6,7-dihydroxy-5. trpyrrolo[l,2-8 ]imidazole-3-carboximidate (29). To a solution of 25 (1 g, 1.8 mmol) in 12 mL of anhydrous MeOH was added NaOH (0.12 g, 2 mmol), and the mixture was stirred at 25 °C for 2 h under nitrogen. The solution was neutralized with Dowex 50 resin (H+) and filtered, and the filtrate was concentrated under reduced pressure. The gummy residue obtained was triturated with dry ether, filtered, and dried to give 0.47 g of product that was homogenous on TLC (CHCl3/MeOH, 4:1). Crystallization from MeOH gave 29 (0.3 g, 64%) as a white powder: mp 182-85

Sphingosine‐1‐phosphate inhibits actin nucleation and pseudopodium formation to control cell motility of mouse melanoma cells

“…Sph was synthesized from the protected serine aldehyde and lithium alkyl derivative [12,13]. N,N.dimothylsphingosine (DMS) was prepared by reductive amination with HCOOH and NaBH4 [14].…”

Towards the synthesis of pyloricidins, synthesis of (2S,3R,4R,5S)-5-amino-2,3,4,6-tetrahydroxyhexanoyl-ß-D-phenyl alanine with differential protective groups

“…6 Grignard reaction of Garner aldehyde 6 with vinylmagnesium bromide in tetrahydrofuran at -78 °C gave the allyl alcohols 8 and 7 with 1:6 syn-anti selectivity. 7 The two diastereomers were separated by silica gel column chromatography.…”

Total Syntheses of FR901464

“…L-threonine was converted to the Garner aldehyde 30 according to the literature. 20 Wittig reaction of this aldehyde with Ph3P= C(Me)CO2Et followed by hydrogenation gave a 2:1 unassigned mixture of diastereomers.…”