89956-14-9Relevant academic research and scientific papers
Prompt determination of absolute configuration for epoxy alcohols via exciton chirality protocol
Li, Xiaoyong,Borhan, Babak
supporting information; experimental part, p. 16126 - 16127 (2009/05/09)
A microscale protocol for determination of absolute configurations of 2,3-epoxy alcohols is described. 2,3-Disubstituted (cis and trans), 2,2-disubstituted, 2,2,3-trisubstituted, and 2,3,3-trisubstituted epoxy alcohols rendered prominent ECCD signals upon complexing with a Lewis acidic porphyrin tweezer and consequently provide straightforward assignment of chirality for epoxy alcohols. This method proved to be rapid, simple, sensitive, and reliable for the class of molecules listed above. Copyright
Stereoselective synthesis of (+)-sordidin, the male-produced aggregation pheromone of the banana weevil Cosmopolites sordidus
Yadav,Reddy, K. Bhaskar,Prasad,Rehman, H. Ur
, p. 2063 - 2070 (2008/09/17)
Stereoselective synthesis of (1S,3R,5R,7S)-(+)-sordidin, the natural male-produced aggregation pheromone of the banana weevil Cosmopolites sordidus (Germar) starting from 5-benzyloxy-(2E)-pentene-1-ol is described. The key transformations employed in the synthesis are Sharpless asymmetric epoxidation, Ueno-Stork cyclization, and Jacobsen kinetic resolution.
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
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
Short synthesis of the 6,6-spiroketal cores of spirofungins A and B
Dias, Luiz C.,De Oliveira, Luciana G.
, p. 2587 - 2590 (2007/10/03)
(Matrix Presented) Initial efforts toward the total synthesis of the antifungal antibiotics spirofungins A and B are reported. A short and efficient synthesis of the C9-C20 6,6-spiroketal fragments of both compounds is described. This asymmetric approach
Enantioselective construction of the C1-C16 segment of lasonolide A
Deba, Tatsuya,Yakushiji, Fumika,Shindo, Mitsuru,Shishido, Kozo
, p. 1500 - 1502 (2007/10/03)
An efficient and enantiocontrolled synthesis of the C1-C 16 segment of lasonolide A has been accomplished starting from a readily available optically pure aldehyde.
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
Pigments of fungi. XLIV* synthesis of differentially protected chiral pentane-1,3,5-triol derivatives; confirmation of the absolute configuration of naturally occurring 3-acetoxy-2,3-dihydropiptoporic acid
Burns, Christopher J.,Gill, Melvyn,Saubern, Simon
, p. 1067 - 1079 (2007/10/03)
(R)-1-t-Butyldimethylsilyloxy-5-phenylmethoxypentan-3-ol (25), prepared in 68% yield and >99.9% enantiomeric excess over six steps from commercially available but-3-yn-1-ol by Katsuki-Sharpless epoxidation, was converted by way of its 3-methoxymethyl ethe
Studies directed towards the synthesis of rapamycin: Stereoselective synthesis of C-1 to C-15 segment
Rama Rao,Desibhatla, Vidyanand
, p. 7111 - 7114 (2007/10/02)
Stereoselective synthesis of a suitably functionalized C-1 to C-15 segment of rapamycin is described.
Total synthesis of the ionophore antibiotic CP-61,405 (routiennocin)
Diez-Martin, David,Kotecha, Nikesh R.,Ley, Steven V.,Mantegani, Sergio,Menendez, J. Carlos,Organ, Helen M.,White, Andrew D.,Banks, Bernard J.
, p. 7899 - 7938 (2007/10/02)
The total synthesis of the spiroketal ionophore antibiotic routiennocin 1 (CP-61,405) employing π-allyltricarbonyl iron lactone complexes is described. These complexes were used as precursors for the preparation of substituted 2-phenylsulphonyl pyrans whi
