106357-25-9Relevant academic research and scientific papers
Preparation of (2R, 3R, 4R)-3-hydroxy-2,4,6-trimethylheptanoic acid via enzymatic desymmertization
Tokairin, Yoshinori,Konno, Hiroyuki
, p. 39 - 45 (2017)
Synthesis of a unique fatty acyl unit to build the N-terminus of callipeltin A and homophymine B is described. Our approach to access (2R, 3R, 4R)-3-hydroxy-2,4,6-trimethylheptanoic acid uses enzymatic hydrolysis for the desymmetrization of achiral acetate, followed by diastereoselective Roush crotylboration and Wittig olefination for the backbone construction.
Step-economic synthesis of (+)-crocacin C: A concise crotylboronation/[3,3] -sigmatropic rearrangement approach
Pasqua, Adele E.,Ferrari, Frank D.,Hamman, Chris,Liu, Yanzhou,Crawford, James J.,Marquez, Rodolfo
, p. 6989 - 6997 (2012/09/25)
The step-economic total synthesis of (+)-crocacin C has been achieved in 20% yield from commercially available starting materials. This approach requires the isolation of only 8 intermediates and can provide a reliable supply of (+)-crocacin C for the development of new antifungal and crop protection agents.
Diastereoselective synthesis of useful building blocks by crotylation of β-branched α-methylaldehydes with potassium crotyltrifluoroborates
Tanaka, Kyosuke,Fujimori, Yukiko,Saikawa, Yoko,Nakata, Masaya
, p. 6292 - 6298 (2008/12/22)
(Chemical Equation Presented) The diastereoselective construction of stereotriads having consecutive methyl, hydroxy, and methyl substituents was realized by the substrate-controlled crotylation of β-branched α-methylaldehydes with potassium crotyltrifluoroborates. Especially, crotylation of 2-(1,3-dithian-2-yl)propanal with potassium (E)- crotyltrifluoroborate afforded, in good yield and with excellent diastereoselectivity, a useful building block that has different and potential functional groups on both ends.
Total synthesis and evaluation of cytostatin, its C10-C11 diastereomers, and additional key analogues: Impact on PP2A inhibition
Lawhorn, Brian G.,Boga, Sobhana B.,Wolkenberg, Scott E.,Colby, David A.,Gauss, Carla-Maria,Swingle, Mark R.,Amable, Lauren,Honkanen, Richard E.,Boger, Dale L.
, p. 16720 - 16732 (2007/10/03)
The total synthesis of cytostatin, an antitumor agent belonging to the fostriecin family of natural products, is described in full detail. The convergent approach relied on a key epoxide-opening reaction to join the two stereotriad units and a single-step
Formal total synthesis of (+)-methynolide
Cossy, Janine,Bauer, David,Bellosta, Véronique
, p. 5909 - 5922 (2007/10/03)
A formal total synthesis of (+)-methynolide was achieved in 23 steps highlighted by a crotylboration, a ring-closing metathesis, a Sharpless kinetic resolution of an allylic alcohol and a Takai reaction.
N,N'-Bis(2,2,2-trifluoroethyl)-N,N'-ethylenetartramide: An Improved Chiral Auxiliary for the Asymmetric Allylboration Reaction
Roush, William R.,Grover, Paul T.
, p. 3806 - 3813 (2007/10/02)
N,N'-Bis(2,2,2-trifluoroethyl)-N,N'-ethylenetartramide (8), synthesized by a simple four-step sequence from ethylenediamine and benzylidenetartaric acid, was designed in anticipation that the derived allylboronates 9-11 would display enhanced reactivity o
Acyclic diastereoselective synthesis using tartrate ester modified crotylboronates. Double asymmetric reactions with α-methyl chiral aldehydes and synthesis of the C(19)-C(29) segment of rifamycin S
Roush, William R.,Palkowitz, Alan D.,Ando, Kaori
, p. 6348 - 6359 (2007/10/02)
Double asymmetric reactions of the tartrate ester modified crotylboronates 1 and 2 and α-methyl chiral aldehydes are described. The reactions of the appropriate enantiomers of 1 and 2 with β-alkoxy-α-methylpropionaldehydes 11 provide adducts 12, 13, and 1
STEREOCHEMICAL CONSEQUENCES FOR THE LEWIS ACID MEDIATED ADDITIONS OF ALLYL AND CROTYLTRI-n-BUTYLSTANNANE TO CHIRAL β-HYDROXYALDEHYDE DERIVATIVES
Keck, Gary E.,Abbott, Duain E.
, p. 1883 - 1886 (2007/10/02)
Proper choice of Lewis acid and hydroxyl protecting group allows for selective addition of crotyltri-n-butylstannane to either face of the aldehyde carbonyl in derivatives of 2-methyl-3-hydroxypropanal with preservation of erythro selectivity for the bond
