title: Regenerative γ-Lactone Annulations: A Modular, Iterative Approach to Oligo-tetrahydrofuran Molecular Stairs and Related Frameworks.
abstract: A unified, stereocontrolled, regenerative γ-butyrolactone annulation approach has been conceptualized and validated through syntheses of a range of oligo-THFs. The new protocol is short (four steps), simple (table-top reagents), and efficient (50-61% overall yields). Although the scope of this approach is unlimited, it has been demonstrated up to five iterations on commercial γ-butyrolactone to assemble six fused tetrahydrofuran moieties in a staircase-like architecture. A selection of exploratory transformations is presented to exemplify the potential applications of this protocol.
authors.affiliation: †Medicinal Chemistry Division, Indian Institute of Integrative Medicine (CSIR), Sanatnagar, Srinagar 190005, India.
authors.forename: Showkat
authors.initials: S
authors.lastname: Rashid
authors.affiliation: †Medicinal Chemistry Division, Indian Institute of Integrative Medicine (CSIR), Sanatnagar, Srinagar 190005, India.
authors.forename: Bilal A
authors.initials: BA
authors.lastname: Bhat
authors.affiliation: ‡School of Chemistry, University of Hyderabad, Hyderabad 500046, India.
authors.forename: Goverdhan
authors.initials: G
authors.lastname: Mehta
mesh_terms: D015107:4-Butyrolactone / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005663:Furans; D007202:Indicators and Reagents; D007783:Lactones; C018674:tetrahydrofuran; D015107:4-Butyrolactone