122137-20-6Relevant articles and documents
Stereoselective synthesis of (+)-boronolide and its 8-epimer
Hu, Shou-Gang,Hu, Tai-Shan,Wu, Yu-Lin
, p. 2305 - 2310 (2004)
The synthesis of (+)-boronolide and its 8-epimer utilizing diastereoselective propargylation of α-hydroxy aldehyde was analyzed. The synthesis process was started with D-tertaric acid converted to diethyl (2S, 3S)-2,3-O-isopropylidenetartrate. A method was established with DIBAL-H as the reducing agent at -78°C to reduce esters directly to aldehydes. Diastereoselective propargylation was shown to be used in the synthesis of structurally diverse compounds.
A facile access to enantiomerically pure [60]fullerene bisadducts with the inherently chiral trans -3 addition pattern
Riala, Maria,Chronakis, Nikos
, p. 2844 - 2847 (2011)
The Bingel reaction between C60 and an enantiopure bismalonate tether equipped with two acetonide moieties led to the synthesis and successful column chromatographic isolation of the enantiomerically pure f,sC and f,sA bisadducts with the inherently chiral trans-3 addition pattern. Acidic deprotection of the acetonide groups gave access to novel chiral fullerene compounds which combine the inherent chirality of the fullerene core with the functional glycol groups located on the tether.
STEREOSELECTIVE SYNTHESIS OF METHYL (1R) TRANS- AND (1R) CIS-HEMICARONALDEHYDES FROM NATURAL TARTARIC ACID: APPLICATION TO THE SYNTHESIS OF S-BIOALLETHRIN AND DELTAMETHRIN INSECTICIDES.
Krief, A.,Dumont, W.,Pasau, P.,Lecomte, Ph.
, p. 3039 - 3052 (1989)
Very efficient enantioselective syntheses of (1R)-trans-and cis-hemicaronaldehydes precursors of (1R)-trans chrysanthemic acid and its (1R)-cis dibromovinyl analogue starting from natural tartaric acid or D-mannitol are described.They are based on the rea
Synthesis and applications of chiral bis-THF in asymmetric synthesis
Alexakis, Alexandre,Tomassini, Axel,Leconte, Stéphane
, p. 9479 - 9484 (2004)
The synthesis of enantiopure bis-THF is described, starting from d-mannitol. Bis-THF is used as chiral ligand for organolithium reagents in four different reactions. The enantioselectivity provided by this ligand is moderate, and the asymmetric induction is in line with the expected model. Graphical Abstract.
A C2-symmetric pool based flexible strategy: An enantioconvergent synthesis of (+)-valiolamine and (+)-valienamine
Lo, Hong-Jay,Chen, Cheng-Yih,Zheng, Wei-Lin,Yeh, Shang-Ming,Yan, Tu-Hsin
experimental part, p. 2780 - 2785 (2012/07/14)
A new enantioconvergent strategy directed toward the synthesis of glucosidase inhibitors was developed by using a C2-symmetric element within the chiral pool and by applying an iodine-promoted cyclization of an unsaturated carbonimidothioate for the regio- and diastereocontrolled installation of amino and hydroxy units. Not only does this simple flexible strategy provide a convergent concise approach to (+)-valiolamine (1), but it can also be readily adopted for the synthesis of (+)-valienamine (2). Commercially available and cheap C2-symmetric D-tartaric acid served as the chiral building block. Copyright
A total synthesis of aliskiren
Nam, Gyeok,Ko, Soo Y.
, p. 1937 - 1945,9 (2012/12/12)
A total synthesis of aliskiren (20) was accomplished. A key in our synthesis was to use the symmetric trans-cisoid-trans-bis-lactone 1 as a precursor. It was expediently prepared by three different routes (Scheme 2). Appending the end groups and functional group transformations completed the synthesis (Scheme 3). Copyright
Chiral pool based efficient synthesis of the aminocyclitol core and furanoside of (-)- hygromycin A: Formal total synthesis of (-)-hygromycin A
Lo, Hong-Jay,Chang, Yuan-Kang,Yan, Tu-Hsin
supporting information, p. 5896 - 5899 (2013/02/23)
A chiral pool based synthetic strategy that leads from the readily available and inexpensive C2-symmetric tartaric acids to the chiral O-isopropylidenebenzooxazolei- a convenient precursor to the aminocyclitol core of hygromycin A as well as the chiral γ-disilyloxybutyrolactone-a pivotal intermediate to approach to the furanoside of hygromycin A.
The enantioselective total synthesis of nemotin
Jian, Ya-Jun,Wu, Yikang
experimental part, p. 811 - 821 (2010/06/20)
The allene-diyne natural product nemotin was synthesized for the first time through an enantioselective route with the stereogenic center at the lactone moiety derived from l-glutamic acid and the allene axis constructed from the corresponding propargylic
An improved two-step synthetic route to primary allylic alcohols from aldehydes
Liu, Zheng,Gong, Yaqiong,Byun, Hoe-Sup,Bittman, Robert
experimental part, p. 470 - 475 (2010/06/14)
An improved two-step synthetic route to allylic alcohols from aldehydes has been developed. A modification of the HWE reaction in H2O-2-PrOH (1 : 1) and a convenient protocol to prepare AlH3 in THF from LiAlH 4 and n-BuBr are the key factors in the improvement.
Asymmetric synthesis of a hydroxylated nine-membered lactone from tartaric acid using the claisen rearrangement
Wong, Leon S.-M.,Turner, Kathleen A.,White, Jonathan M.,Holmes, Andrew B.,Ryan, John H.
scheme or table, p. 529 - 532 (2010/08/03)
The synthesis of a hydroxylated vinyl-appended lactone, in five synthetic steps from tartaric acid, is reported. The C2-symmetrical bis-vinyl diol 12 was converted into the ketene acetal 14 via methylenation of the cyclic carbonate 13 or thermal elimination of benzeneselenenic acid from the selenoxide 17. In both cases, the in situ generated ketene acetal 14 underwent spontaneous Claisen rearrangement to give the nine-membered lactone (+)-15. Lactones of this type are potentially advanced precursors to simplified eleutherobin analogues or other medium-ring lactone natural products.
