Total synthesis of ent-dioxepandehydrothyrsiferol via a bromonium-initiated epoxide-opening cascade.
In the first total synthesis of ent-dioxepandehydrothyrsiferol, the signature trans-anti-trans 7,7,6-fused tricyclic polyether framework was constructed in a single bromonium-initiated epoxide-opening cascade that incorporates both endo- and exo-selective epoxide openings, each directed by the substitution pattern of the epoxide (methyl groups). This study thus demonstrates the feasibility of a possible biogenesis.
Tanuwidjaja
Jessica
J
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Ng
Sze-Sze
SS
Jamison
Timothy F
TF
D001966:Bromine / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D005240:Feasibility Studies; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D004852:Epoxy Compounds; D006575:Heterocyclic Compounds, 3-Ring; C545060:dioxepandehydrothyrsiferol; D001966:Bromine