- Model study toward total synthesis of dimeric pyranonaphthoquinones: Synthesis of hemi-actinorhodin#
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In connection with our synthetic study toward the dimeric pyranonaphthoquinone antibiotics, actinorhodin (1) and β-naphthocyclinone (3), we describe herein the synthesis of a monomer, hemi-actinorhodin (6) as a model target. Several implications were gained, including (1) stereoselective synthesis of the pyranonaphthoquinone, (2) viable construction of the naphthazarin core, and (3) the final deprotection conditions.
- Ando, Yoshio,Fukazawa, Takumi,Ohmori, Ken,Suzuki, Keisuke
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supporting information
p. 1364 - 1376
(2021/05/17)
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- Atroposelective Total Synthesis of the Fourfold ortho-Substituted Naphthyltetrahydroisoquinoline Biaryl O,N-Dimethylhamatine
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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
- Slack, Eric D.,Seupel, Raina,Aue, Donald H.,Bringmann, Gerhard,Lipshutz, Bruce H.
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supporting information
p. 14237 - 14245
(2019/11/11)
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- Total Synthesis of Eleuthoside A; Application of Rh-Catalyzed Intramolecular Cyclization of Diazonaphthoquinone
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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.
- Othman, Dina I. A.,Otsuka, Kota,Takahashi, Shuhei,Selim, Khalid B.,El-Sayed, Magda A.,Tantawy, Atif S.,Okauchi, Tatsuo,Kitamura, Mitsuru
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supporting information
p. 457 - 462
(2018/02/23)
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- SYNTHESIS OF THE POTENT IMMUNOSUPPRESSANT AGENTS DALESCONOL A AND B
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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.
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Page/Page column 62
(2011/09/19)
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- Total syntheses of dalesconol A and B
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(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.
- Snyder, Scott A.,Sherwood, Trevor C.,Ross, Audrey G.
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supporting information; experimental part
p. 5146 - 5150
(2010/11/04)
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- Lewis acid-promoted cyclization of heteroatom-substituted enynes.
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Lewis acid-promoted cyclizations of heteroatom-substituted enynes have been examined. The reaction of enynes and bearing silicon substituents on an alkyne afforded the halogenated five-membered gamma-lactones and gamma-lactams as the main products. The reaction of substrates and having 2-phosphonoacrylate instead of malonate also gave halogenated five-membered cyclic compounds and as the major products. The cyclized products are highly substituted and potentially useful for further synthetic transformations.
- Yamazaki, Shoko,Yamada, Kuriko,Yamamoto, Kagetoshi
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p. 257 - 264
(2007/10/03)
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- Asymmetric synthesis of an MMP-3 inhibitor incorporating a 2-alkyl succinate motif
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An efficient and practical synthesis is presented of the pharmaceutically active MMP-3 inhibitor UK-370,106 (1) via an olefination/catalytic asymmetric hydrogenation sequence. Commercially available 5-bromo-2-iodotoluene was converted in two steps to the
- Ashcroft, Christopher P.,Challenger, Stephen,Derrick, Andrew M.,Storey, Richard,Thomson, Nicholas M.
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p. 362 - 368
(2013/09/06)
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- A new synthesis of Rhein
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A novel synthesis of Rhein (2), the active metabolite of the anti-osteoarthritic drug Diacetyl Rhein (1) has been achieved. Key steps include stereospecific olefination of aldehyde 21 with novel phosphonate 28 and the cylisation of acid 31 to produce anthracene 32.
- Gallagher, Peter T.,Hicks, Terry A.,Lightfoot, Andrew P.,Martin Owton
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p. 289 - 292
(2007/10/02)
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- tert-Butyl-3-carboxyethyl-3-phosphonodiethylpropionate. A novel reagent for Stobbe-like condensations
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tert-Butyl-3-carboxyethyl-3-phosphonodiethylpropionate was prepared and reacted with a range of aldehydes to give, after hydrolysis, itaconic half esters.
- Owton,Gallagher,Juan-Montesinos
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p. 2119 - 2125
(2007/10/02)
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- A general approach to substituted itaconate esters
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A general approach to the synthesis of various itaconates including 3-substituted esters is presented. The complementarity of the approach is also shown.
- Dowd,Wilk
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p. 2307 - 2322
(2007/10/02)
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- A SHORT SYNTHESIS OF THE Δ1-CARBOPENEM RING SYSTEM
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Michael addition of N-lithio-4-vinyl-azetidin-2-one to several vinyl phosphonates gave adducts which were converted to Δ1-carbopenems via ozonolysis and an intramolecular Horner-Wittig reaction.
- Venugopalan, B.,Hamlet, A. Bevin,Durst, Tony
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p. 191 - 194
(2007/10/02)
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