Asymmetric synthesis of fagomine

Stereoselective Aminopalladation and Oxypalladation and Their Application to the Synthesis of Natural Products

“…Fagomine (3) exhibits inhibitory activity against mammalian -glucosidase and glucosidase, respectively [13]. In 2007, Hirai and co-workers accomplished an asymmetric synthesis of 3 via Sharpless asymmetric dihydroxylation [14] and aminopalladation [15]. 3-(t-Butoxycarbonylamino)propanol ( 15) was used as a starting material.…”

Modular Construction of Protected 1,2/1,3-Diols, -Amino Alcohols, and -Diamines via Catalytic Asymmetric Dehydrative Allylation: An Application to Synthesis of Sphingosine

“…(E)-But-2-ene-1,4-diol (2) was purchased from TCI and purified by silica-gel column chromatography before use or synthesized from but-2-yne-1,4-diol according to ref 16. N-Boc-aminomethanol (4), 17 N-Cbz-aminomethanol, 18 N-Bz-aminomethanol, 19 N-pivaloylaminomethanol, 20 N-trifluoroacetylaminomethanol, 21 N,N′-bistosylaminal, 22 (E)-pent-2-ene-1,5-diol (6), 23 (E)-N-Boc-4-aminobut-2-en-1-ol ( 7), 24 and (E)-N-Boc-5-aminopent-2-en-1-ol ( 8) 25 were synthesized according to the reported methods.…”

Catalytic Asymmetric Cycloadditions between Aldehydes and Enolizable Anhydrides: cis-Selective Dihydroisocoumarin Formation

“…1 tert-Butyl (3-Oxopropyl)carbamate (S3). Synthesized according to the procedure developed by Fujisawa et al 24 An oven-dried 50 mL round-bottomed flask containing a magnetic stirring bar under an argon atmosphere was charged with a solution of DMSO (3 mL, 32.3 mmol) in CH 2 Cl 2 (57 mL), followed by oxalyl chloride (1.4 mL, 16.1 mmol) at −78 °C. The resultant mixture was stirred for 15 min, and a solution of S2(1.71 g, 10.7 mmol) in CH 2 Cl 2 (50 mL) was added dropwise.…”