89923-31-9Relevant academic research and scientific papers
An efficient stereoselective total synthesis of 11β-methoxycurvularin
Yadav,Vani, C. Divya,Bhasker,Reddy, B.V. Subba
, p. 291 - 300 (2014/10/15)
A very short and efficient stereoselective total synthesis of a macrocyclic ketone, 11β-methoxycurvularin was achieved by employing the Sharpless asymmetric epoxidation, formation of propargyl alcohols from an epoxy-chloride, and intramolecular Friedel-Cr
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
Concise total synthesis of dihydrocorynanthenol, protoemetinol, protoemetine, 3-epi-protoemetinol and emetine
Lin, Shuangzheng,Deiana, Luca,Tseggai, Abrehet,Cordova, Armando
, p. 398 - 408 (2012/02/16)
A concise asymmetric assembly of secologanine tryptamine and dopamine alkaloids by means of a one-pot three-component cascade reaction methodology is disclosed. This is demonstrated by the expeditious total syntheses of (-)-dihydrocorynanthenol, (-)-protoemetinol, (-)-protoemetine, (-)-3-epi-protoemetinol, and emetine (3-6 steps). The biomimetic synthetic strategy involved the following key steps: (i) One-pot three-component highly enantioselective catalytic Michael/Pictet-Spengler/lactamization cascade reactions; (ii) One-pot tandem Swern oxidation/Wittig sequences; (iii) One-pot tandem hydrogenation sequences. Copyright
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
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 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
Primary and secondary allyltitanium(IV) reagents in aldehyde allylation II: Application to an enantioselective preparation of a C1-C7 fragment of spiramycin
Razon, Patrick,N'Zoutani, Marie-Ange,Dhulut, Sylvie,Bezzenine-Lafollee, Sophie,Pancrazi, Ange,Ardisson, Janick
, p. 109 - 121 (2007/10/03)
A synthetic approach to the eastern part of spiramycin, an important antibiotic compound, is described. Introduction of the side chain was first envisaged through a Hoppe aldehyde allylation. This reaction was carried out between an optically pure aldehyde 32 and a (±)-γ-alkoxy allyltitanium(IV) species derived from a primary γ-alkoxy allyl (diisopropyl)carbamate. Under kinetic resolution conditions, the anti-Cram compound 35 was obtained in an 80:20 mixture, with the Cram isomer 34, in 81% yield. Employing the optically pure (S)-γ-alkoxy allyl (diisopropyl)carbamate 36, the corresponding (R)-γ-alkoxy allyltitanium (R)-'Ti'-III was generated under n-BuLi·TMEDA/Ti(Oi-Pr)4 conditions, that reacted with aldehyde 32 in double stereodifferentiation to deliver the expected Cram compound 40 in 80% yield (95% de). This latter corresponded to the C1-C7 fragment of spiramycin.
Synthesis of the ABCD and ABCDE ring systems of azaspiracid-1
Zhou, Xiao-Ti,Carter, Rich G.
, p. 2138 - 2140 (2007/10/03)
The efficient syntheses of the ABCD ring system of the originally proposed structure of azaspiracid-1 and the ABCDE ring system of the revised structure of azaspiracid-1 containing the correct stereochemistry at C6, C 10, Q3, C14, C16, C17, C19, C21, C22, C24 and C 25 have been achieved.
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
Enantio- and stereocontrolled formation of the bisspiroacetal core of spirolide B
Ishihara, Jun,Ishizaka, Tomoko,Suzuki, Takanori,Hatakeyama, Susumi
, p. 7855 - 7858 (2007/10/03)
The bisspiroacetal core of spirolide B, a marine natural toxin, was synthesized from triketone 10 via one-step bisspiroacetalization, methylation, and silylation accompanied by isomerization of the C-15 spirocenter. The equilibrium of two isomers under ac
