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Synthesis 2006(18): 3015-3018
DOI: 10.1055/s-2006-942547
DOI: 10.1055/s-2006-942547
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Stereoselective Anti-Aldol Route to (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol: A Key Ligand for a New Generation of HIV Protease Inhibitors
Further Information
Publication History
Received
27 April 2006
Publication Date:
02 August 2006 (online)


Abstract
A stereoselective synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol, an important high affinity P2-ligand, in high enantiomeric excess (>99%) is reported. The synthesis features an ester-derived titanium enolate based highly stereoselective anti-aldol reaction as the key step.
Key Words
antiviral agents - asymmetric synthesis - chiral auxiliary - aldol reactions - fused-ring systems