title: The stereoselective synthesis of cis-/trans-fused hexahydropyrano[4,3-b]chromenes via Prins cyclization trapping by a tethered nucleophile.
abstract: A novel intramolecular Prins cyclization of (Z)-2-(5-hydroxypent-2-enyl)phenol with various aldehydes has been achieved using 10 mol% In(OTf)(3) and 30 mol% TsOH to produce the cis-fused hexahydropyrano[4,3-b]chromene derivatives in good yields, while the coupling of (E)-2-(5-hydroxypent-2-enyl)phenol with aldehydes under similar conditions affords the corresponding trans-fused hexahydropyrano[4,3-b]chromene derivatives.
authors: Natural Product Chemistry, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500607, India. basireddy@iict.res.in
authors: B V Subba
authors: BV
authors: Reddy
authors: Sayed
authors: S
authors: Jalal
authors: Prashant
authors: P
authors: Borkar
authors: J S
authors: JS
authors: Yadav
authors: P P
authors: PP
authors: Reddy
authors: A C
authors: AC
authors: Kunwar
authors: B
authors: B
authors: Sridhar
mesh_terms: D000962:Antimalarials / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000962:Antimalarials; D001578:Benzopyrans; D011714:Pyrans