72586-64-2Relevant academic research and scientific papers
Total Synthesis of Eleuthoside A; Application of Rh-Catalyzed Intramolecular Cyclization of Diazonaphthoquinone
Othman, Dina I. A.,Otsuka, Kota,Takahashi, Shuhei,Selim, Khalid B.,El-Sayed, Magda A.,Tantawy, Atif S.,Okauchi, Tatsuo,Kitamura, Mitsuru
, p. 457 - 462 (2018)
The first total synthesis of (±)-eleutherol and eleuthoside A, the natural cytotoxic substances extracted from medicinal Indonesian plant, is described. First, the synthesis of (±)-eleutherol has been accomplished in nine steps starting from bromo methoxy aldehyde with the aid of diazo-transfer chemistry approach. Second, a metal-catalyzed intramolecular cyclization reaction of the corresponding diazonaphthoquinone led to the desired eleuotherol, which served as a precursor to eleuthoside A. Then, several glycosidation routes, using different glucosyl donors, were experimented to reach effective O-glycosidation of eleutherol. The only successful strategy involved Koenigs-Knorr glycosidation using peracetyl glycosyl bromide in the presence of Ag 2 O and quinoline. This strategy furnished our desired acetylated glycoside of β-configuration, regioselectively. Finally, deacetylation and successive separation of diastereomers were conducted to give eleuthoside A.
Atroposelective Total Synthesis of the Fourfold ortho-Substituted Naphthyltetrahydroisoquinoline Biaryl O,N-Dimethylhamatine
Slack, Eric D.,Seupel, Raina,Aue, Donald H.,Bringmann, Gerhard,Lipshutz, Bruce H.
supporting information, p. 14237 - 14245 (2019/11/11)
A stereoselective total synthesis of O,N-dimethylhamatine, an analogue of an axially chiral naphthylisoquinoline natural biaryl product from tropical Ancistrocladus lianas, is reported. The route features a late-stage atropo-diastereoselective biaryl bond
SYNTHESIS OF THE POTENT IMMUNOSUPPRESSANT AGENTS DALESCONOL A AND B
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Page/Page column 7; 63, (2011/09/19)
This invention relates to compounds having the structure: wherein bonds α, β, γ, δ, ω, η, χ, ε, κ, and μ are each present or absent, and R1-R18 are various substituents described herein.
Total syntheses of dalesconol A and B
Snyder, Scott A.,Sherwood, Trevor C.,Ross, Audrey G.
supporting information; experimental part, p. 5146 - 5150 (2010/11/04)
(Chemical equation Presented) (Chemical equation Presented) A polycyclic collapse: Use of a carefully designed acyclic intermediate participated in a cascade reaction that formed the entire core of the polyketide-derived dalesconols in a single flask (see scheme). A number of additional and carefully controlled synthetic operations completed an expeditious synthesis of both of these highly bioactive natural products as well as structural congenors.
