Efficient synthesis of 3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol from glycolaldehyde
A one-step diastereoselective (up to 98:2) synthesis of the bis-furan alcohol of Darunavir and other HIV drug candidates has been achieved utilizing the novel cyclizatlon of glycolaldehyde and 2,3-dihydrofuran. The cycloaddition was catalyzed by a variety of catalysts including those formed from tin(II) triflate and common chiral ligands such as BINAP and Evans's box ligands. An efficient and unique enzymatic process enhanced the enantiomeric purity to provide the target in optically pure form.
Canoy, Will L.,Cooley, Bob E.,Corona, John A.,Lovelace, Thomas C.,Millar, Alan,Weber, Aimee M.,Xie, Shiping,Zhang, Yong
scheme or table
p. 1103 - 1106
(2009/04/06)
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