Efficient synthesis of 3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol from glycolaldehyde

Organic Letters

Volumn 10, Issue 6, 2008, Pages 1103-1106

  Canoy, Will L ^a   Cooley, Bob E ^a   Corona, John A ^a   Lovelace, Thomas C ^a   Millar, Alan ^a   Weber, Aimee M ^a   Xie, Shiping ^a   Zhang, Yong ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; FURAN DERIVATIVE; HEXAHYDROFURO(2,3 B)FURAN 3 OL; HEXAHYDROFURO(2,3-B)FURAN-3-OL; LIGAND;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ANTI-HIV AGENTS; CATALYSIS; CYCLIZATION; FURANS; LIGANDS; STEREOISOMERISM;

EID: 45549097437     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol703061u     Document Type: Article

References (29)

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27. Typical procedure for screening reactions: a catalyst, 5 mol % relative to 2,3-DHF unless otherwise noted, was prepared by mixing a metal salt (0.068 mmol) and a ligand (0.071 mmol) in 1.5 mL of solvent (2:1 of DCM and another solvent when mixture used) at ambient temperature for 40 min. Glycolaldehyde dimer (86 mg, 0.71 mmol) was added in one portion. The resultant solution was cooled with an ice bath, followed by addition of 2,3-DHF (100 mg, 1.43 mmol). The reaction was warmed to ambient temperature over about one hour and sampled for analysis upon completion, typically within 5 h.
28. All reactions were sampled by evaporation to remove solvents, diluted with MeCN and directly injected to chiral GC for ratio analysis.
29. 3c