70542-83-5Relevant articles and documents
Synthesis of Panal Terpenoid Core
Baranov, Mikhail S.,Kaskova, Zinaida M.,Gritсenko, Roman,Postikova, Svetlana G.,Ivashkin, Pavel E.,Kislukhin, Alexander A.,Moskvin, Dmitrii I.,Mineev, Konstantin S.,Arseniev, Alexander S.,Labas, Yulii A.,Yampolsky, Ilia V.
supporting information, p. 583 - 588 (2017/03/11)
Panal is a natural bicyclic cadalane-type sesquiterpenoid with an unusual combination of stereocenters. It was isolated in 1988 as an alleged biosynthetic precursor of luciferin (a light-emitting molecule) in a bioluminescent fungus Panellus stipticus. Herein we present the first approach to the synthesis of the terpenoid skeleton of panal, which includes construction of five stereocenters, one of which is easily epimerizable. The key steps in the synthetic approach presented are high-pressure Diels-Alder reaction disobeying the ‘endo rule’, Barbier reductive allylation, and cyclization of trans-decalin ring via ring-closing metathesis.
AMINO PYRAZOLONE DERIVATIVE HAVING CONDENSED RING STRUCTURE
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Paragraph 0227; 0228; 0229; 0231, (2016/10/08)
PROBLEM TO BE SOLVED: To provide a compound that has excellent inhibitory action on ATPase activity of TIP48/TIP49 complex and is therefore useful for the treatment of tumor, or a pharmacologically acceptable salt thereof. SOLUTION: The present invention provides a compound having a structure represented by general formula (I), its pharmacologically acceptable salt, or a pharmaceutical composition comprising the compound (where R3, R4, R5, R6, R7, W, X, Y, and Z are as defined in the specifications). SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
Enantioselective synthesis of the natural product (S)-rugulactone
Nagaiah, Burea,Narsaiah, Akkirala Venkat
, p. 1948 - 1954 (2013/11/06)
A simple and efficient enantioselective synthesis of (6S)-5,6-dihydro-6- [(2E)-4-oxo-6-phenylhex-2-en-1-yl]-2H-pyran-2-one (=(S)-rugulactone) has been accomplished. The synthesis started from commercially available propane-1,3-diol and ethyl 3-phenylpropa
Synthesis of the FG ring fragment of pectenotoxins 1-9
Heapy, Amanda M.,Brimble, Margaret A.
scheme or table, p. 5424 - 5431 (2010/08/13)
The synthesis of the FG ring fragment common to pectenotoxins 1-9 is reported.The successful, convergent synthesis relied on high yielding routes to access two key intermediates; aldehyde 1 and phosphonium salt 2.A Z-selective Wittig reaction gave access
Total synthesis of (-)-ulapualide A, a novel tris-oxazole macrolide from marine nudibranchs, based on some biosynthesis speculation
Pattenden, Gerald,Ashweek, Neil J.,Baker-Glenn, Charles A. G.,Kempson, James,Walker, Gary M.,Yee, James G. K.
scheme or table, p. 1478 - 1497 (2008/10/09)
A new, second generation, total synthesis of ulapualide A (1), whose stereochemistry was recently determined from X-ray analysis of its complex with the protein actin, is described. The synthesis is designed and based on some speculation of the biosynthet
Synthesis of the FG fragment of the pectenotoxins
Heapy, Amanda M.,Wagner, Thomas W.,Brimble, Margaret M.
, p. 2359 - 2362 (2008/03/13)
The synthesis of the FG subunit of the pectenotoxins is reported herein. The synthesis hinges on the preparation of an appropriately functionalized acyclic precursor using a Z-selective Wittig reaction. Further elaboration using two sequential cyclization
Diastereomerically and enantiomerically pure 2,3-disubstituted pyrrolidines from 2,3-aziridin-1-ols using a sulfoxonium ylide: A one-carbon homologative relay ring expansion
Schomaker, Jennifer M.,Bhattacharjee, Somnath,Yan, Jun,Borhan, Babak
, p. 1996 - 2003 (2007/10/03)
An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring-closure yields the desired pyrrolidine, thus completing the relay of the three-membered to the five-membered nitrogen-containing ring system. This process takes place with complete transfer of stereochemical fidelity and can be applied to sterically hindered aziridinols.
Synthesis of diastereomerically and enantiomerically pure 2,3-disubstituted tetrahydrofurans using a sulfoxonium ylide
Schomaker, Jennifer M.,Pulgam, Veera Reddy,Borhan, Babak
, p. 13600 - 13601 (2007/10/03)
Nucleophilic substitution reactions of 2,3-epoxy alcohols, easily prepared via Sharpless asymmetric epoxidation chemistry, offer access to a wide variety of enantiomerically pure compounds. In this communication, we describe the use of a Payne rearrangement to control regioselectivity in the ring-opening of a series of 2,3-epoxy alcohols with dimethylsulfoxonium methylide to yield diastereomerically and/or enantiomerically pure disubstituted tetrahydrofuran rings. The factors influencing the success and substitution pattern of the THF ring products are discussed, including steric, electronic, and solvent effects. Copyright
Application of oxazolidinone α-fluoro amide chiral building blocks in the asymmetric synthesis of fluorinated carbohydrates: 2-Deoxy-2-fluoropentoses
Davis, Franklin A.,Qi, Hongyan,Sundarababu, Gajendran
, p. 5303 - 5310 (2007/10/03)
Deconjugative electrophilic fluorination of the lithium dienolate of Z-α,β-unsaturated imide (+)-9 with N-fluorobenzene-sulfonimide (NFSi) afforded the E-β,γ-unsaturated α-fluoro imide (+)-10 as a single diastereoisomer. Dihydroxylation resulted in the formation of 2-fluoro-2-deoxy-γ-xylonic and -lyxonic lactones, 12a and 12b, respectively. Reduction and deprotection of the lactones afforded 2-deoxy-2-fluoro-xylo-D-pyranose (15) and 2-deoxy-2-fluoro-lyxo-L-pyranose (17). (C) 2000 Elsevier Science Ltd.
A total synthesis of the unique tris-oxazole macrolide ulapualide a produced by the marine nudibranch Hexabranchus sanguineus
Chattopadhyay, Shital K.,Pattenden, Gerald
, p. 2429 - 2454 (2007/10/03)
A total synthesis of ulapualide A (1), whose relative stereochemistry was assigned on the basis of an earlier molecular mechanics study of its hypothetical metal chelated complex 9, is described. The synthesis is based on: i, elaboration of the double fun
