307492-71-3Relevant academic research and scientific papers
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
experimental part, 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.
Formal synthesis of (+)-crocacin C
Pasqua, Adele E.,Ferrari, Frank D.,Crawford, James J.,Marquez, Rodolfo
, p. 2114 - 2116 (2012/07/13)
The formal synthesis of (+)-crocacin C is reported. The approach described takes advantage of a highly regioselective epoxide cuprate addition and a diastereoselective Overman rearrangement. The synthesis is practical and amenable to scale up.
Total synthesis of (+)-crocacin C
Sirasani, Gopal,Paul, Tapas,Andrade, Rodrigo B.
scheme or table, p. 3648 - 3655 (2010/08/03)
Two approaches toward the total synthesis of cytotoxic polyketide natural product (+)-crocacin C (1) are described. The first approach, which was ultimately unsuccessful, was replaced altogether with a second that afforded target 1 in 10 linear steps from commercially available Evans' chiral propionimide (5% overall yield). No protecting groups were utilized in the total synthesis of 1.
Asymmetric total synthesis of the myxobacteria metabolites crocacins A-D
Feutrill, John T.,Lilly, Michael J.,White, Jonathan M.,Rizzacasa, Mark A.
, p. 4880 - 4895 (2008/09/21)
The total syntheses of crocacins A-D are described. The key steps were a syn-aldol reaction followed by anti-reduction to secure the stereotetrad and acylation of an ene- or dienecarbamate to form the enamide. Crown Copyright
Concise total synthesis of (+)-crocacin C
Sirasani, Gopal,Paul, Tapas,Andrade, Rodrigo B.
, p. 6386 - 6388 (2008/12/22)
(Chemical Equation Presented) The cytotoxic natural product (+)-crocacin C (1) has been synthesized in 10 linear steps from commercially available Evans' chiral propionimide in 5% overall yield (8 steps from Evans' chiral dipropionate synthon). No protect
A formal total synthesis of crocacin C
Yadav,Reddy, P. Venkatram,Chandraiah
, p. 145 - 148 (2007/10/03)
An efficient total synthesis of a potent antifungal and moderate cytotoxic agent crocacin C is described. The synthesis involves the generation of four contiguous stereogenic centres via desymmetrization of a meso bicyclic dihydrofuran using asymmetric hy
Stereoselective formal synthesis of crocacin C via prins cyclization
Yadav,Sridhar Reddy,Purushothama Rao,Prasad
, p. 2049 - 2052 (2008/02/09)
A formal synthesis of crocacin C is described proving the versatility of Prins cyclization in natural product synthesis. The approach is convergent and highly stereoselective. Cross-metathesis and Heck reactions were utilized for the insertion of an aroma
Total synthesis of (+)-crocacin D
Dias, Luiz C.,De Oliveira, Luciana G.,Vilcachagua, Janaina D.,Nigsch, Florian
, p. 2225 - 2234 (2007/10/03)
(Chemical Equation Presented) The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moie
Carbohydrate-based synthesis of crocacin: Stereoselective Heck reaction of carbohydrate 5,6-ene- and 5,6-yne-derivatives with aromatic halides
Gurjar, Mukund K.,Khaladkar, Tushar P.,Borhade, Ramdas G.,Murugan
, p. 5183 - 5187 (2007/10/03)
The Heck reaction between a carbohydrate 5,6-ene derivative 9 and an aromatic halide exclusively gave rise to the β-carbohydrate-substituted trans-styrene derivative 8; while the corresponding Wittig reaction produced a cis/trans mixture in which the cis-
Total synthesis of (+)-crocacin D
Feutrill, John T.,Lilly, Michael J.,Rizzacasa, Mark A.
, p. 525 - 527 (2007/10/03)
(formula presented) The first asymmetric synthesis of (+)-crocacin D (4) is described. The key steps in the sequence are the stereoselective assembly of the stereotetrad via a substrate-controlled aldol reaction and anti-selective reduction, formation of
