106357-27-1Relevant articles and documents
Electrochemical and photochemical approaches for the synthesis of the C28–C38 fragment of okadaic acid
Dochain, Simon,Nshimyumuremyi, Jean-Boris,Dewez, Damien F.,Body, Jean-Fran?ois,Elias, Benjamin,Singleton, Michael L.,Markó, István E.
, p. 2280 - 2283 (2019)
Okadaic acid, a potent and selective inhibitor of Protein Phosphatases 1 and 2A (PP1 and PP2A), is widely used as a probe for various biochemical processes. We describe herein two innovative methods for the synthesis of the terminal C28–C38 fragment of the natural polyether. Suárez photochemical oxidative cyclization and electrochemical oxidation of malonates to their ketals equivalents have been successfully applied for the assembly of the key spiroketal core.
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.
Total synthesis of (-)-spongidepsin
Ferrie, Laurent,Reymond, Sebastien,Capdevielle, Patrice,Cossy, Janine
, p. 3441 - 3443 (2007/10/03)
A convergent and rapid stereoselective synthesis of (-)-spongidepsin has been achieved from the Roche ester in 14 steps with an overall yield of 13%.
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.
Formation of dissymmetric eight-membered silalketals by ring-closing metathesis and their conversion to spiroketals
Boiteau, Jean-Guy,Van De Weghe, Pierre,Eustache, Jacques
, p. 239 - 242 (2007/10/03)
Eight-membered unsymmetrical silalketals are formed by RCM of mixed allyl/homoallyl silalketals. They are crucial intermediates in a short synthetic sequence to spiroketals illustrated in this paper by the synthesis of the C28-C38 po
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.
