91548-58-2Relevant academic research and scientific papers
Stereoselective Synthesis of the C27-C35 Eribulin Fragment and Its Utilization in Building Structurally Diverse Macrocycles
Konda, Saidulu,Khatravath, Mahender,Mallurwar, Naveen Kumar,Rao, Pallavi,Sripelly, Shivashankar,Iqbal, Javed,Arya, Prabhat
, p. 1663 - 1683 (2016/05/24)
A practical and scalable stereoselective synthesis of the western substituted tetrahydrofuran ring C27-C35 fragment of eribulin was developed by using (2S,3S)-tartaric acid as a cheap starting material that was converted into an intermediate through a stereoselective vinylation and cross-metathesis as the key steps. A regio-and stero-selective intramolecular oxy-Michael cyclization or an iodocyclization reaction finally provided the required western tetrahydrofuran ring fragment and its related isomeric analogues. These key fragments were further utilized in obtaining several types of macrocyclic derivatives for exploration of their biological properties. The simplicity of our present approach has the potential to be considered for large-scale syntheses of key fragments of eribulin and related analogues.
Stereoselective synthesis of tetrahydropyran-tetrahydrofuran (THP-THF) core of (+)-muconin via Prins cyclization
Yadav,Reddy, U.V. Subba,Reddy, B.V. Subba
, p. 3860 - 3863 (2014/07/08)
A stereoselective synthesis of tetrahydropyran-tetrahydrofuran (THP-THF) core 2 of (+)-muconin (1) has been achieved using Prins cyclization as a key step to construct tetrahydropyran moiety. Other important transformations such as Wittig olefination, Sharpless epoxidation, regio-, and stereoselective exo-cyclization of the epoxy alcohol, titanocene induced regioselective deoxygenation of 2,3-epoxy alcohol, Grignard reaction, and Barton-McCombie reaction are successfully employed to accomplish the synthesis of THP-THF core 2.
A new stereoselective total synthesis of phomonol
Subba Reddy, Basi V.,Srinivas, Lavudia,Reddy, Pathuri Sivaramakrishna,Reddy, Bhemavarapu Phaneendra,Prasad, Attaluri R.,Yadav, Jhillu S.
, p. 1326 - 1332 (2015/04/16)
A stereoselective total synthesis of phomonol, following organocatalytic enantioselective epoxidation and intramolecular oxa-Michael reaction as key steps, is described. The use of readily available dtartaric acid as a chiral source renders this approach
DIBAL-mediated reductive transformation of trans-dimethyl tartrate acetonide into ε-hydroxy α,β-unsaturated ester and its derivatives
Tomioka, Takashi,Yabe, Yuki,Takahashi, Tohru,Simmons, Tracy K.
, p. 4669 - 4674 (2011/07/30)
Stepwise, selective DIBAL reduction of the acetonide diester derived from tartaric acid followed by the Horner- Emmons reaction effectively provided desymmetrized hydroxy mono-olefination products in a one-pot operation.
Synthesis of the C3-14 fragment of palmerolide A using a chiral pool based strategy
Lebar, Matthew D.,Baker, Bill J.
experimental part, p. 1557 - 1562 (2010/04/02)
Palmerolide A, a potent and selective inhibitor of melanoma cell growth, is a macrocylic polyketide isolated from the Antarctic tunicate Synoicum adareanum. Palmerolide A targets transmembrane proton pumps, the vacuolar-ATPases, and induces autophagy, but
A New Method for the Dehydration of β-Hydroxy Sulfones: Synthesis of (E,S)-γ-Hydroxy-α,β-unsaturated Sulfones and (S)-ε-Hydroxy-(E,E)-α,γ-dienyl Sulfones
Kang, Suk-Ku,Park, Young-Won,Kim, Sung-Gyu,Jeon, Jae-Hoon
, p. 405 - 406 (2007/10/02)
Optically active (E,S)-γ-hydroxy-α,β-unsaturated sulfones and (S)-ε-hydroxy-(E,E)-α,γ-dienyl sulfones have been prepared in a one-pot dehydration procedure from β,γ-dihydroxy sulfones and δ,ε-dihydroxy allyl sulfones, respectively, via an elimination reac
An acyl radical initiated tandem 7-endo/5-exo radical cyclization approach to enantiomerically pure bicyclo[5.3.0]decan-2-ones
Batty,Crich
, p. 875 - 878 (2007/10/02)
The preparation of acetonide derivatives of erythro and threo 4,5-dihydroxyhept-6-enoic acids from the chiral pool is described. The phenylseleno esters derived from these acids undergo cyclization with tributyltin hydride to give mixtures of cyclohexanones and cycloheptanones. The inclusion of the appropriate four carbon side chain at C-7 leads, via a tandem radical cyclization process, to the title compounds in moderate yield.
4-O-Benzyl-23-O-isopropylidene-L-threose: A useful building block for stereoselective synthesis of monosaccharides
Mukaiyama, Teruaki,Suzuki, Keisuke,Yamada, Tohru,Tabusa, Fujio
, p. 265 - 276 (2007/10/02)
4-O-Benzyl-23-O-isopropylidene-L-threose readily available from L-tartaric acid is a quite useful four-carbon building block for monosaccharide synthesis. The versatility can be reinforced by the coupled use of stereoselective addition reactions where the
CONJUGATE ADDITION REACTION OF TRIMETHYLSILYLACETONITRILE WITH Α,Β-UNSATURATED CARBONYL COMPOUNDS. SYNTHETIC STUDIES TOWARD SESBANIMIDE
Tomioka, Kiyoshi,Koga, Kenji
, p. 1599 - 1600 (2007/10/02)
Lithiated trimethylsilylacetonitrile was allowed to react with some α,β-unsaturated carbonyl compounds to give the corresponding conjugate addition products.
