5233-99-8Relevant articles and documents
van Broekhoven,L.W. et al.
, p. 2909 - 2910 (1974)
Organocatalytic epoxidation and allylic oxidation of alkenes by molecular oxygen
Orfanidou, Maria,Petsi, Marina,Zografos, Alexandros L.
supporting information, p. 9172 - 9178 (2021/11/30)
Pyrrole-proline diketopiperazine (DKP) acts as an efficient mediator for the reduction of dioxygen by Hantzsch ester under mild conditions to allow the aerobic metal-free epoxidation of electron-rich alkenes. Mechanistic crossovers are underlined, explaining the dual role of Hantzsch ester as a reductant/promoter of the DKP catalyst and a simultaneous competitor for the epoxidation of alkenes when HFIP is used as a solvent. Expansion of this protocol to the synthesis of allylic alcohols was achieved by adding a catalytic amount of selenium dioxide as an additive, revealing a superior method to the classical application of t-BuOOH as a selenium dioxide oxidant.
Relay Cross Metathesis for the Iterative Construction of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic Relevance to the Bromophycolides
Bahou, Karim A.,Braddock, D. Christopher,Meyer, Adam G.,Savage, G. Paul
supporting information, p. 3176 - 3179 (2020/04/15)
We report a relay cross metathesis (ReXM) reaction for the construction of terpenoids in an iterative protocol. The protocol features the cross metathesis of a relay-actuated Δ6,7-functionalized C10-monoterpenoid alcohol with C10-monoterpenoid citral to form a C15-sesquiterpene. Subsequent functional group manipulation allows for the method to be repeated in an iterative fashion. The method is used for the synthesis of a diterpene-benzoate macrolide of biogenetic relevance to the bromophycolide family of natural products.
Biomimetic cyclization of epoxide precursors of indole mono-, sesquiand diterpene alkaloids by lewis acids
Isaka, Tetsuya,Hasegawa, Morifumi,Toshima, Hiroaki
experimental part, p. 2213 - 2222 (2012/02/14)
Cyclization of the synthesized epoxide precursors of indole mono-, sesqui- and diterpene alkaloids was performed to elucidate the mechanism for biomimetic cationic cyclization to polycyclic structures. 3-(6,7- Epoxygeranyl)indole (11), 3-(10,11-epoxyfarne