Stereoselective Synthesis of cis-Fused Perhydrofuro[2,3-b]furan Derivatives from Sugar-Derived Allyl Vinyl Ethers

A stereoselective methodology has been developed for the construction of cis‐fused perhydrofuro[2,3‐b]furans, via 3‐C‐branched glycal derivatives, involving Claisen rearrangement of sugar‐derived allyl vinyl ethers, followed by a one‐pot ozonolysis and acid‐mediated acetalization. The methodology wa...

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Bibliographic Details
Published in:European journal of organic chemistry 2012-11, Vol.2012 (31), p.6228-6235
Main Authors: Sridhar, Perali Ramu, Reddy, Gadi Madhusudhan, Seshadri, Kalapati
Format: Article
Language:English
Subjects:
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiviral agents
Biological and medical sciences
Carbohydrates
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Chiral pool
Cyclization
Derivatives
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
HIV
Human immunodeficiency virus
Medical sciences
Organic chemistry
Oxygen heterocycles
Pharmacology. Drug treatments
Preparations and properties
Protease inhibitors
Sigmatropic rearrangement
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Summary:A stereoselective methodology has been developed for the construction of cis‐fused perhydrofuro[2,3‐b]furans, via 3‐C‐branched glycal derivatives, involving Claisen rearrangement of sugar‐derived allyl vinyl ethers, followed by a one‐pot ozonolysis and acid‐mediated acetalization. The methodology was used for the stereoselective synthesis of the P2 ligand in the recently FDA approved HIV protease inhibitor darunavir (Prezista). The methodology was also successfully used for the synthesis of cis‐fused perhydro‐5‐oxofuro[2,3‐b]furan derivatives. A general protocol for the stereoselective synthesis of cis‐fused perhydrofuro[2,3‐b]furans has been developed using carbohydrates as chiral‐pool starting materials. Depending on the precursor sugar, this procedure can provide any stereoisomer of the bis‐THF system in a stereoselective fashion. The extension of the methodology for the synthesis of perhydro‐5‐oxofuro[2,3‐b]furans is also reported.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201200898