- Synthesis method of novel hexahydrofuro[2,3-b]furan chloronicotinyl insecticide
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The invention provides a synthesis method for preparing novel hexahydrofuro[2,3-b]furan chloronicotinyl insecticide (compounds V). Hexahydrofuro[2,3-b]furan-3-ol serves as the initial raw materials, an activated ester substrate is generated through an est
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Paragraph 0030; 0031; 0032
(2016/10/07)
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- Stereoselective synthesis of cis-fused perhydrofuro[2,3-b]furan derivatives from sugar-derived allyl vinyl ethers
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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.
- Sridhar, Perali Ramu,Reddy, Gadi Madhusudhan,Seshadri, Kalapati
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p. 6228 - 6235
(2013/01/15)
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- Stereoselective photochemical 1,3-dioxolane addition to 5-alkoxymethyl-2(5H)-furanone: Synthesis of bis-tetrahydrofuranyl ligand for HIV protease inhibitor UIC-94017 (TMC-114)
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A convenient synthesis of (3R,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan, a high-affinity non-peptidal ligand for HIV protease inhibitor UIC-94017, is described. This inhibitor is undergoing advanced clinical trials. The synthesis utilizes a novel stereoselective photochemical 1,3-dioxolane addition to 5(S)-benzyloxymethyl-2(5H)-furanone as the key step. The requisite furanone derivative was prepared in high enantiomeric excess by an immobilized lipase-catalyzed selective acylation of (±)-1-(benzyloxy)-3-buten-2-ol and a ring-closing olefin metathesis with Grubbs' catalyst. Optically active bis-THF was converted to protease inhibitor 2 (UIC-94017).
- Ghosh, Arun K.,Leshchenko, Sofiya,Noetzel, Marcus
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p. 7822 - 7829
(2007/10/03)
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