A Regio- and Stereocontrolled Synthesis of (+)-Isocarbacyclin via (1S,2R,5R)-Bicyclo[3.3.0]oct-6-en-endo-2-ol

Hashimoto, Shinya; Kase, S.; Shinoda, Tomohiro; Ikegami, Shiro

doi:10.1246/cl.1989.1063

Cited by 14 publications

(2 citation statements)

References 17 publications

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“…18 Exposure of 11 to iodine in the presence of silver acetate in acetic acid afforded the corresponding iodoacetate derivative. 19 Reduction of the resulting iodoacetate with LAH furnished hydroxy benzyl ether 12 20 in 50% yield in two steps. The hydroxyl group in 12 was protected as TBSether by reaction with TBSCl and imidazole.…”

Section: Chemistrymentioning

confidence: 99%

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Structure-Based Design of Novel HIV-1 Protease Inhibitors To Combat Drug Resistance

et al. 2006

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Structure-based design and synthesis of novel HIV protease inhibitors are described. The inhibitors are designed specifically to interact with the backbone of HIV protease active site to combat drug resistance. Inhibitor 3 has exhibited exceedingly potent enzyme inhibitory and antiviral potency. Furthermore, this inhibitor maintains impressive potency against a wide spectrum of HIV including a variety of multi-PI-resistant clinical strains. The inhibitors incorporated a stereochemically defined 5-hexahydrocyclopenta[b]furanyl urethane as the P2-ligand into the (R)-(hydroxyethylamino)sulfonamide isostere. Optically active (3aS,5R,6aR)-5-hydroxy-hexahydrocyclopenta[b]furan was prepared by an enzymatic asymmetrization of meso-diacetate with acetyl cholinesterase, radical cyclization, and Lewis acid-catalyzed anomeric reduction as the key steps. A protein-ligand X-ray crystal structure of inhibitor 3-bound HIV-1 protease (1.35 A resolution) revealed extensive interactions in the HIV protease active site including strong hydrogen bonding interactions with the backbone. This design strategy may lead to novel inhibitors that can combat drug resistance.

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Section: Chemistrymentioning

confidence: 99%

“…Benzyl ether 11 was synthesized according to the literature procedure . Exposure of 11 to iodine in the presence of silver acetate in acetic acid afforded the corresponding iodoacetate derivative . Reduction of the resulting iodoacetate with LAH furnished hydroxy benzyl ether 12 in 50% yield in two steps.…”

Section: Chemistrymentioning

confidence: 99%