106357-26-0Relevant articles and documents
Preparation of (2R, 3R, 4R)-3-hydroxy-2,4,6-trimethylheptanoic acid via enzymatic desymmertization
Tokairin, Yoshinori,Konno, Hiroyuki
, p. 39 - 45 (2016/12/09)
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.
Synthetic studies toward C3-C9 segment of Soraphen A1α
Eweas, Ahmad Farouk
, p. 1541 - 1552 (2008/09/21)
The ring-closure metathesis of the diene (2S,3R,4S)-1-(tert- butyldiphenylsilyloxy)-2,4-dimethylhex-5-en-3-yl acrylate produced the dihydropyrone with the correct stereochemistry for Soraphen A1α synthesis. The C2,C3 stereocenters were introduced by the a
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
Total synthesis of cytostatin
Lawhorn, Brian G.,Boga, Sobhana B.,Wolkenberg, Scott E.,Boger, Dale L.
, p. 65 - 70 (2007/10/03)
The total synthesis of cytostatin, an antitumor agent belonging to the fostriecin family of natural products, is disclosed. The convergent route features a key epoxide opening reaction to join the two stereotriad units and a single-step late stage, stereo
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.
Enantioselective and Diastereoselective Additions of Allylic Stannanes to Aldehydes Promoted by a Chiral (Acyloxy)borane Catalyst
Marshall, James A.,Palovich, Michael R.
, p. 4381 - 4384 (2007/10/03)
A modified Yamamoto Lewis acid (CAB), prepared from the 2,6-dimethoxybenzoic ester of (R,R)- tartaric acid, and 1.5 equiv of BH3-THF was employed in additions of crotyltributyltin (6) and allyltributyltin (9) to representative achiral aldehydes in the presence of 2 equiv of (CF3CO)2O. The crotyltin additions proceeded with good to excellent diastereoselectivity and enantioselectivity affording the syn adducts 7a-e of 70-90% ee as major products (78:22-92:8). Addition of allylstannane 9 to cyclohexanecarboxaldehyde (1a) afforded the (R)-adduct of only 55% ee. In contrast, the use of Keek's BINOL catalyst gave 10, the allyl adduct of 1a, of 87% ee. However, addition of the crotylstannane to 1a with this catalyst led to a 65:35 mixture of syn and anti adducts 7a and 8a of 95% and 49% ee. Additions of crotylstannane 6 to (R)- and (S)-2-methyl-3-ODPS- propanal [(R)-11 and (S)-11] promoted by the modified CAB Lewis acid afforded the syn,syn and syn,anti products 12 and 14 in large predominance (98:2 and 90:10), indicative of effective complex control in the transition state. The results are consistent with the Corey H-bonded aldehyde transition-state proposal.
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
