title: Construction of the tricyclic furanochroman skeleton of phomactin A via the Prins/Conia-ene cascade cyclization approach.
abstract: A substrate-controlled asymmetric Prins/Conia-ene cascade cyclization has been developed with In(OTf)(3) in CH(3)CN from 0 to 70 °C. These conditions afforded very good yields of the 1-oxadecalin product in one pot and effectively suppressed the racemization of the 1-oxadecalin product with almost no enantiomeric excess (ee) loss. This cascade cyclization has been successfully employed for the construction of the highly functionalized 1-oxadecalin unit of phomactin A with an acyclic β-keto ester and an alkynal as the substrates via a one-pot operation (66% yield, single diastereomer). The 1-oxadecalin moiety has been readily converted to the tricyclic furanochroman skeleton of phomactin A via the epoxidation/dealkoxycarbonylation protocol under very mild conditions with 52% yield in three steps.
authors: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen University Town, Xili, Shenzhen 518055, China.
authors: Shuangping
authors: S
authors: Huang
authors: Guangyan
authors: G
authors: Du
authors: Chi-Sing
authors: CS
authors: Lee
mesh_terms: D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002839:Chromans; D004852:Epoxy Compounds; D005663:Furans; D006576:Heterocyclic Compounds, 4 or More Rings; D009281:Naphthalenes; C491966:furanochroman; C449320:oxadecalin; C413206:phomactin A