title: Stereoselective Synthesis of Hexahydro-1H-spiro[isoquinoline-4,4'-pyran] Scaffolds through an Intramolecular Prins Cascade Process.
abstract: A novel tandem cyclization strategy has been developed for the synthesis of hexahydro-1H-spiro[isoquinoline-4,4'-pyran] derivatives through the condensation of 3-((benzylamino)methyl)but-3-en-1-ol with aldehydes using BF3·OEt2. The reaction proceeds in a highly stereoselective manner, leading to a single diastereoisomer. This approach is a simple and efficient alternative for the synthesis of pharmacologically important spiroisoquinoline scaffolds.
authors.affiliation: †Natural Product Chemistry and ‡Laboratory of X-ray Crystallography, Academy of Scientific and Innovative Research, Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: B V
authors.initials: BV
authors.lastname: Subba Reddy
authors.affiliation: †Natural Product Chemistry and ‡Laboratory of X-ray Crystallography, Academy of Scientific and Innovative Research, Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: Durgaprasad
authors.initials: D
authors.lastname: Medaboina
authors.affiliation: †Natural Product Chemistry and ‡Laboratory of X-ray Crystallography, Academy of Scientific and Innovative Research, Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: B
authors.initials: B
authors.lastname: Sridhar
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D003500:Cyclization; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001880:Boranes; D007546:Isoquinolines; D011714:Pyrans; C000599577:hexahydro-1H-spiro(isoquinoline-4,4'-pyran); C101707:boron trifluoride etherate