title: Concise approach to the carbocyclic core of the naturally occurring sphingomyelinase inhibitor scyphostatin.
abstract: A flexible strategy toward the carbocyclic core of the naturally occurring sphingomyelinase inhibitor scyphostatin, from the readily available Diels-Alder adducts of cyclopentadiene and 2-allyl-p-benzoquinone, has been devised. This approach leverages the stereochemical predisposition of the norbornyl-fused scaffolds to generate the desired stereochemical pattern and leads to a concise synthesis of the epoxycyclohexenoid core of scyphostatin with a manipulable allyl side arm.
authors: School of Chemistry, University of Hyderabad, Hyderabad 500 046, India. gm@orgchem.iisc.ernet.in
authors: Goverdhan
authors: G
authors: Mehta
authors: Nagi Reddy
authors: NR
authors: Modugu
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D008968:Molecular Conformation; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013108:Sphingomyelin Phosphodiesterase / Q000037:antagonists & inhibitors / Q000378:metabolism
chemical_list: D000577:Amides; D004791:Enzyme Inhibitors; D011753:Pyrones; C121123:scyphostatin; D013108:Sphingomyelin Phosphodiesterase