title: Stereoselective synthesis of octahydrocyclohepta[c]pyran-6(1H)-one scaffolds through a Prins/alkynylation/hydration sequence.
abstract: Aldehydes undergo a smooth coupling with (E/Z)-non-3-en-8-yn-1-ol in the presence of 10 mol% of CuX and BF3·OEt2 under mild conditions to produce a novel class of octahydrocyclohepta[c]pyran-6(1H)-one derivatives in good yields with excellent diastereoselectivity through a sequential Prins/alkynylation/hydration. This is the first report on the termination of Prins cyclization with a tethered alkyne.
authors: Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Tarnaka, 500 007, Hyderabad, India. basireddy@iict.res.in.
authors: A
authors: A
authors: Venkateswarlu
authors: M
authors: M
authors: Kanakaraju
authors: Ajit C
authors: AC
authors: Kunwar
authors: B V Subba
authors: BV
authors: Reddy
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D003500:Cyclization; D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000480:Alkynes; D003508:Cycloheptanes; D011753:Pyrones; C000606453:octahydrocyclohepta(c)pyran-6(1H)-one